Monster Maker application in Tkinter

Question

I have a program that works okay (not fully completed) however, I would like to simplify things and create some classes and different .py files for my tkinter app as I feel that would help organize everything better. I think where the confusion for me lies is how does each .py file class or function call to the main window/mainloop and get written to it?

How would you go about organizing this?

Code:

from doctest import master
import string
import tkinter
import tkinter.messagebox
import customtkinter
from tkinter import *
import random

#TODO Create IF statement for Saves based on stats
#TODO Create healthpool options
#TODO Fix error messages to show any value in list already exists

customtkinter.set_appearance_mode("System")  # Modes: "System" (standard), "Dark", "Light"
customtkinter.set_default_color_theme("blue")  # Themes: "blue" (standard), "green", "dark-blue"

class App(customtkinter.CTk):

    WIDTH = 1450
    HEIGHT = 900
    monster_stat_list = [
                            "Monster Name",
                            "Size",
                            "Monster Type",
                            "AC Type",
                            "AC",
                            "HP",
                            "Speed",
                            "Extra Move Type",
                            "STR",
                            "DEX",
                            "CON",
                            "INT",
                            "WIS",
                            "CHA",
                            "Saves",
                            "Skills",
                            "Vulnerabilities",
                            "Immunities",
                            "Resistances",
                            "Senses",
                            "Languages",
                            "Special Traits",
                            "Actions",
                            "Legendary Actions",
                            "Lair Actions",
                            "Spells"
                        ]

    def __init__(self):
        super().__init__()

        self.title("Monster Maker")
        self.geometry(f"{App.WIDTH}x{App.HEIGHT}")
        
        #------------Setup Frame---------------#
        # configure grid layout (2x1)
        self.grid_columnconfigure(1, weight=1)
        self.grid_rowconfigure(0, weight=1)
        #configure left frame
        self.frame_left = customtkinter.CTkFrame(master=self,
                                                 width=180,
                                                 corner_radius=0)
        self.frame_left.grid(row=0, column=0, sticky="nswe", padx=10,pady=10)
        #configure right frame
        self.frame_right = customtkinter.CTkFrame(master=self)
        self.frame_right.grid(row=0, column=1, sticky="nswe", padx=10, pady=10)
        #Far Left Frame
        self.frame_left.grid_rowconfigure(0, minsize=10)   # empty row with minsize as spacing        
        
        #-----------Generate Button function --------------#
        #Create a generate function for button 
        def generate_monster():
            pass

        #Create Generate Button
        generate_monster_button = customtkinter.CTkButton(master=self.frame_left, 
                                                        text="Generate Monster", 
                                                        command=generate_monster,
                                                        text_font=("Roboto Medium", 16))
        generate_monster_button.grid(row=0, column=0, columnspan = 4, padx=5,pady=10)
        
        #----------- Create Monster Options ------------#
                #--------Monster Name---------#
        monster_name_entry = customtkinter.CTkEntry(master=self.frame_right, placeholder_text='Enter Name')
        monster_name_entry.grid(row=0,column=1)
        monster_name = monster_name_entry.get()
        print(monster_name)

                        #-------Size--------#
        #Size Combobox
        size_label = customtkinter.CTkLabel(master=self.frame_left, text="Size Option")
        size_label.grid(row=1,column=0)
        size_options_combobox = ["Random", "Tiny", "Small", "Medium", "Large", "Huge", "Gargantuan"]
        size_options_label = ["Tiny", "Small", "Medium", "Large", "Huge", "Gargantuan"]
        size_combobox = customtkinter.CTkComboBox(master=self.frame_left, values=size_options_combobox)
        size_combobox.grid(row=1, column=1)
        size_combobox.set("Random")
        current_size = size_combobox.current_value
        #Add size function
        def add_size():
            size_choice = StringVar()
            size_choice = size_combobox.get()
            random_size = random.choice(size_options_label)
            if size_choice == "Random":
                display_size['text'] = random_size
                
            else:
                display_size['text'] = size_choice
            
            
        # #Display Size
        display_size = customtkinter.CTkLabel(master=self.frame_right, text='')
        display_size.grid(row=1,column=1)
        
        #Create button to add a size
        add_size_btn = customtkinter.CTkButton(master=self.frame_left, text="Add Size", command=add_size)
        add_size_btn.grid(row=1, column=2)

                             #-------Monster Type--------#
        #Monster type Combobox
        monster_type_label = customtkinter.CTkLabel(master=self.frame_left, text="Monster Type Option")
        monster_type_label.grid(row=2,column=0)
        monster_type_options_combobox = ["Random","Aberration", "Beast", 
                        "Celestial", "Construct", "Dragon", 
                        "Elemental", "Fey", "Fiend", 
                        "Giant", "Humanoid", "Monstrosity", 
                        "Ooze", "Plant", "Undead"
                        ]
        monster_type_options_label = ["Aberration", "Beast", 
                        "Celestial", "Construct", "Dragon", 
                        "Elemental", "Fey", "Fiend", 
                        "Giant", "Humanoid", "Monstrosity", 
                        "Ooze", "Plant", "Undead"
                        ]
        monster_type_combobox = customtkinter.CTkComboBox(master=self.frame_left, values=monster_type_options_combobox)
        monster_type_combobox.grid(row=2, column=1)
        monster_type_combobox.set("Random")
        current_monster_type = monster_type_combobox.current_value
        #Add Monster Type function
        def add_monster_type():
            monster_type_choice = StringVar()
            monster_type_choice = monster_type_combobox.get()
            monster_random_type = random.choice(monster_type_options_label)
            if monster_type_choice == "Random":
                display_monster_type['text'] = monster_random_type
            else:
                display_monster_type['text'] = monster_type_choice
        #Display Type
        display_monster_type = customtkinter.CTkLabel(master=self.frame_right, text='')
        display_monster_type.grid(row=2,column=1)
        #Create button to add a monster type
        add_monster_type_btn = customtkinter.CTkButton(master=self.frame_left, text="Add Type", command=add_monster_type)
        add_monster_type_btn.grid(row=2, column=2)

                        # ---------------- AC Options --------------#
        #AC type Combobox
        ac_type_label = customtkinter.CTkLabel(master=self.frame_left, text="AC Type Option")
        ac_type_label.grid(row=3,column=0)
        ac_type_options_combobox = ["Random", "Ancestral", "Magic", "Natural", "Worn"]
        ac_type_options_label = ["Ancestral", "Magic", "Natural", "Worn"]
        ac_type_combobox = customtkinter.CTkComboBox(master=self.frame_left, values= ac_type_options_combobox)
        ac_type_combobox.grid(row=3, column=1)
        ac_type_combobox.set("Random")
        current_ac_type = ac_type_combobox.current_value
        #Add AC Type function
        def add_ac_type():
            ac_type_choice = StringVar()
            ac_type_choice = ac_type_combobox.get()
            random_ac_type = random.choice(ac_type_options_label)
            if ac_type_choice == "Random":
                display_ac_type['text'] = random_ac_type
            else:
                display_ac_type['text'] = ac_type_choice
        #Display AC Type
        display_ac_type = customtkinter.CTkLabel(master=self.frame_right, text='')
        display_ac_type.grid(row=3,column=1)
        #Create button to add a AC Type
        add_ac_type_btn = customtkinter.CTkButton(master=self.frame_left, text="Add AC Type", command=add_ac_type)
        add_ac_type_btn.grid(row=3, column=2)
        
                                #---------AC Value--------#
        #AC Value Combobox
        ac_value_label = customtkinter.CTkLabel(master=self.frame_left, text="AC Value Option")
        ac_value_label.grid(row=4,column=0)
        ac_value_options_combobox = ["Random",
                    "7","8","9","10",
                    "11","12","13","14",
                    "15","16","17","18",
                    "19","20","21","22",
                    "23","24","25","26",
                    ]
        ac_value_options_label = [
                    "7","8","9","10",
                    "11","12","13","14",
                    "15","16","17","18",
                    "19","20","21","22",
                    "23","24","25","26",
                    ]
        ac_value_combobox = customtkinter.CTkComboBox(master=self.frame_left, values= ac_value_options_combobox)
        ac_value_combobox.grid(row=4, column=1)
        ac_value_combobox.set("Random")
        current_ac_value = ac_value_combobox.current_value

        #Add AC Value function
        def add_ac_value():
            ac_value_choice = StringVar()
            ac_value_choice = ac_value_combobox.get()
            random_ac_value = random.choice(ac_value_options_label)
            if ac_value_choice == "Random":
                display_ac_value['text'] = random_ac_value
            else:
                display_ac_value['text'] = ac_value_choice
        #Display AC Value
        display_ac_value = customtkinter.CTkLabel(master=self.frame_right, text='')
        display_ac_value.grid(row=4,column=1)
        #Create button to add AC Value
        add_ac_value_btn = customtkinter.CTkButton(master=self.frame_left, text="Add AC Value", command=add_ac_value)
        add_ac_value_btn.grid(row=4, column=2)



                    # ---------------- HP Pool Option --------------#
        hp_pool_options = {"Low" : (
                        "5","10","15","20",
                        "25","30","35","40",
                        "45","50","55","60",
                        "65","70","75","80",
                        "85","90","95","100"),

                    "Medium" : (
                        "105","110","115","120",
                        "125","130","135","140",
                        "145","150","155","160",
                        "165","170","175","180",
                        "185","190","195","200",),

                    "High" : (
                        "205","210","215","220",
                        "225","230","235","240",
                        "245","250","255","260",
                        "265","270","275","280",
                        "285","290","295","300",),

                    "Extreme" : (
                        "325","350","375","400",
                        "425","450","475","500",
                        "525","550","575","600",
                        "625","650","675","700",
                        "725","750","775","800",)}
        
        def on_pool_selected(hp_value):
            hp_values = ('Random',)
            if hp_value == 'Random':
                for v in hp_pool_options.values():
                    hp_values += v
            else:
                hp_values += hp_pool_options[hp_value]
            hp_value_combobox.configure(values=hp_values)
            hp_value_combobox.set('Random')
            
        
        #Label
        hp_pool_label = customtkinter.CTkLabel(master=self.frame_left, text="HP Option")
        hp_pool_label.grid(row=5,column=0)
        hp_var1 = customtkinter.StringVar()
        hp_pool_combobox = customtkinter.CTkComboBox(master=self.frame_left, 
                                        variable=hp_var1, 
                                        values=("Random",)+tuple(hp_pool_options.keys()), 
                                        command=on_pool_selected)
        hp_pool_combobox.grid(row=5, column=1)
        

        hp_var2 = customtkinter.StringVar()
        hp_value_combobox = customtkinter.CTkComboBox(master=self.frame_left, variable=hp_var2)
        hp_value_combobox.grid(row=5, column=2)
        hp_value_combobox.set("Random")
        hp_pool_combobox.set("Random")
        
        # #TODO
        # #Add HP Value function
        # def add_hp_value():
        #     hp_value_choice = StringVar()
        #     hp_value_choice = hp_value_combobox.get()
        #     random_hp_value = random.choice(hp_values)
        #     if hp_value_choice == "Random":
        #         display_hp_value['text'] = random_hp_value
        #     else:
        #         display_hp_value['text'] = hp_value_choice

        #Display HP Value
        display_hp_value = customtkinter.CTkLabel(master=self.frame_right, text='')
        display_hp_value.grid(row=5,column=1)
        #Create button to add HP Value
        add_hp_value_btn = customtkinter.CTkButton(master=self.frame_left, text="Add HP Value") #TODO , command=add_hp_value()
        add_hp_value_btn.grid(row=5, column=3)

                            # ----------Movement Options ------------#
        # Base Movement Speed Combobox
        move_speed_label = customtkinter.CTkLabel(master=self.frame_left, text="Base Move Speed Option")
        move_speed_label.grid(row=6,column=0)
        move_speed_options_combobox = ["Random", 
                                        "10 ft","20 ft","30 ft",
                                        "40 ft","50 ft","60 ft",
                                        "70 ft","80 ft","90 ft",
                                        "100 ft","110 ft","120 ft"
                                        ]
        move_speed_options_label = [
                                        "10 ft","20 ft","30 ft",
                                        "40 ft","50 ft","60 ft",
                                        "70 ft","80 ft","90 ft",
                                        "100 ft","110 ft","120 ft"
                                        ]
        move_speed_combobox = customtkinter.CTkComboBox(master=self.frame_left, values=move_speed_options_combobox)
        move_speed_combobox.grid(row=6, column=1)
        move_speed_combobox.set("Random")
        current_move_speed = move_speed_combobox.current_value
        #Add Move Speed function
        def add_move_speed():
            move_speed_choice = StringVar()
            move_speed_choice = move_speed_combobox.get()
            random_move_speed = random.choice(move_speed_options_label)
            if move_speed_choice == "Random":
                display_move_speed['text'] = random_move_speed
            else:
                display_move_speed['text'] = move_speed_choice
        #Display Move Speed
        display_move_speed = customtkinter.CTkLabel(master=self.frame_right, text='')
        display_move_speed.grid(row=6,column=1)
        #Create button to add Move Speed
        add_move_speed_btn = customtkinter.CTkButton(master=self.frame_left, text="Add Move Speed", command=add_move_speed)
        add_move_speed_btn.grid(row=6, column=2)

                    # ------------Extra Move Type /Speed --------------#
        #Extra Movement Type Combobox
        extra_move_type_label = customtkinter.CTkLabel(master=self.frame_left, text="Extra Move Type Option")
        extra_move_type_label.grid(row=7,column=0)
        extra_move_type_options_combobox = ["Random", "Burrow", "Climb", "Fly", "Swim"]
        extra_move_type_options_label = [ "Burrow", "Climb", "Fly", "Swim"]
        extra_move_type_combobox = customtkinter.CTkComboBox(master=self.frame_left, values=extra_move_type_options_combobox)
        extra_move_type_combobox.grid(row=7, column=1)
        extra_move_type_combobox.set("Random")
        current_extra_move_type = extra_move_type_combobox.current_value
        #Create list of move speeds
        extra_move_list = []    

        #Add Extra Move Type function
        def add_extra_move_type():
            #Type
            extra_move_type_choice = StringVar()
            extra_move_type_choice = extra_move_type_combobox.get()
            random_extra_move_type = random.choice(extra_move_type_options_label)
            #Speed
            extra_move_speed_choice = StringVar()
            extra_move_speed_choice = extra_move_speed_combobox.get()
            random_extra_move_speed = random.choice(extra_move_speed_options_label)

            if any(extra_move_type_choice in s for s in extra_move_list):
                tkinter.messagebox.showinfo('Error', f'{extra_move_type_choice} Movement type already added.')
            else:                              
                if extra_move_type_choice == "Random" and extra_move_speed_choice == "Random":
                    extra_move_list.append(random_extra_move_type + ' ' + random_extra_move_speed)
                    display_extra_move_type['text'] = ' | '.join(extra_move_list)
                                                
                elif extra_move_type_choice == "Random" and extra_move_speed_choice != "Random":
                    extra_move_list.append(random_extra_move_type + ' ' + extra_move_speed_choice)
                    display_extra_move_type['text'] = ' | '.join(extra_move_list)

                elif extra_move_type_choice !="Random" and extra_move_speed_choice == "Random":
                    extra_move_list.append(extra_move_type_choice + ' ' + random_extra_move_speed)
                    display_extra_move_type['text'] = ' | '.join(extra_move_list)

                elif extra_move_type_choice !="Random" and extra_move_speed_choice != "Random":
                    extra_move_list.append(extra_move_type_choice + ' ' + extra_move_speed_choice)
                    display_extra_move_type['text'] = ' | '.join(extra_move_list)

        #Extra Speed
        extra_move_speed_options_combobox = ["Random", 
                            "10 ft","20 ft","30 ft",
                            "40 ft","50 ft","60 ft",
                            "70 ft","80 ft","90 ft",
                            "100 ft","110 ft","120 ft"
                            ]
        extra_move_speed_options_label = [ 
                            "10 ft","20 ft","30 ft",
                            "40 ft","50 ft","60 ft",
                            "70 ft","80 ft","90 ft",
                            "100 ft","110 ft","120 ft"
                            ]
        extra_move_speed_combobox = customtkinter.CTkComboBox(master=self.frame_left, values=extra_move_speed_options_combobox)
        extra_move_speed_combobox.grid(row=7, column=2)
        extra_move_speed_combobox.set("Random")
        current_extra__move_speed = extra_move_speed_combobox.current_value
        

        #Display Extra Move Speed
        display_extra_move_type = customtkinter.CTkLabel(master=self.frame_right, text='')
        display_extra_move_type.grid(row=7,column=1)
        #Create button to add Move Extra Speed
        add_extra_move_type_btn = customtkinter.CTkButton(master=self.frame_left, text="Add Extra Movement",command=add_extra_move_type )#
        add_extra_move_type_btn.grid(row=7, column=3)

        


                        # ---------- Monster Stats --------- #
        #Stats options
        stats_options_combobox = [
            "Random",
            "1","5","6","7","8",
            "9","10","11","12","13",
            "14","15","16","17","18",
            "19","20","21","22","23",
            "24","25","26","27","28",
            "29","30",
        ]
        stats_options_label = [
            "1","5","6","7","8",
            "9","10","11","12","13",
            "14","15","16","17","18",
            "19","20","21","22","23",
            "24","25","26","27","28",
            "29","30",
        ]

        #STR Combobox
        str_label = customtkinter.CTkLabel(master=self.frame_left, text="STR Option")
        str_label.grid(row=9,column=0)
        str_combobox = customtkinter.CTkComboBox(master=self.frame_left, values=stats_options_combobox)
        str_combobox.grid(row=9, column=1)
        str_combobox.set("Random")
        current_str = str_combobox.current_value
        #Add str Value function
        def add_str():
            str_choice = StringVar()
            str_choice = str_combobox.get()
            random_str = random.choice(stats_options_label)
            if str_choice == "Random":
                display_str['text'] = random_str
            else:
                display_str['text'] = str_choice
        #Display STR Value
        display_str = customtkinter.CTkLabel(master=self.frame_right, text='')
        display_str.grid(row=9,column=1)
        #Create button to add STR Value
        add_str_btn = customtkinter.CTkButton(master=self.frame_left, text="Add STR Value", command=add_str)
        add_str_btn.grid(row=9, column=2)

        #DEX Combobox
        dex_label = customtkinter.CTkLabel(master=self.frame_left, text="DEX Option")
        dex_label.grid(row=10,column=0)
        dex_combobox = customtkinter.CTkComboBox(master=self.frame_left, values=stats_options_combobox)
        dex_combobox.grid(row=10, column=1)
        dex_combobox.set("Random")
        current_dex = dex_combobox.current_value
        #Add DEX Value function
        def add_dex():
            dex_choice = StringVar()
            dex_choice = dex_combobox.get()
            random_dex = random.choice(stats_options_label)
            if dex_choice == "Random":
                display_dex['text'] = random_dex
            else:
                display_dex['text'] = dex_choice
        #Display DEX Value
        display_dex = customtkinter.CTkLabel(master=self.frame_right, text='')
        display_dex.grid(row=10,column=1)
        #Create button to add DEX Value
        add_dex_btn = customtkinter.CTkButton(master=self.frame_left, text="Add DEX Value", command=add_dex)
        add_dex_btn.grid(row=10, column=2)

        #CON Combobox
        con_label = customtkinter.CTkLabel(master=self.frame_left, text="CON Option")
        con_label.grid(row=11,column=0)
        con_combobox = customtkinter.CTkComboBox(master=self.frame_left, values=stats_options_combobox)
        con_combobox.grid(row=11, column=1)
        con_combobox.set("Random")
        current_con = con_combobox.current_value
        #Add con Value function
        def add_con():
            con_choice = StringVar()
            con_choice = con_combobox.get()
            random_con = random.choice(stats_options_label)
            if con_choice == "Random":
                display_con['text'] = random_con
            else:
                display_con['text'] = con_choice
        #Display con Value
        display_con = customtkinter.CTkLabel(master=self.frame_right, text='')
        display_con.grid(row=11,column=1)
        #Create button to add con Value
        add_con_btn = customtkinter.CTkButton(master=self.frame_left, text="Add Con Value", command=add_con)
        add_con_btn.grid(row=11, column=2)

        #INT Combobox
        int_label = customtkinter.CTkLabel(master=self.frame_left, text="INT Option")
        int_label.grid(row=12,column=0)
        int_combobox = customtkinter.CTkComboBox(master=self.frame_left, values=stats_options_combobox)
        int_combobox.grid(row=12, column=1)
        int_combobox.set("Random")
        current_int = int_combobox.current_value
        #Add int Value function
        def add_int():
            int_choice = StringVar()
            int_choice = int_combobox.get()
            random_int = random.choice(stats_options_label)
            if int_choice == "Random":
                display_int['text'] = random_int
            else:
                display_int['text'] = int_choice
        #Display int Value
        display_int = customtkinter.CTkLabel(master=self.frame_right, text='')
        display_int.grid(row=12,column=1)
        #Create button to add int Value
        add_int_btn = customtkinter.CTkButton(master=self.frame_left, text="Add INT Value", command=add_int)
        add_int_btn.grid(row=12, column=2)

        #WIS Combobox
        wis_label = customtkinter.CTkLabel(master=self.frame_left, text="WIS Option")
        wis_label.grid(row=13,column=0)
        wis_combobox = customtkinter.CTkComboBox(master=self.frame_left, values=stats_options_combobox)
        wis_combobox.grid(row=13, column=1)
        wis_combobox.set("Random")
        current_wis = wis_combobox.current_value
        #Add wis Value function
        def add_wis():
            wis_choice = StringVar()
            wis_choice = wis_combobox.get()
            random_wis = random.choice(stats_options_label)
            if wis_choice == "Random":
                display_wis['text'] = random_wis
            else:
                display_wis['text'] = wis_choice
        #Display wis Value
        display_wis = customtkinter.CTkLabel(master=self.frame_right, text='')
        display_wis.grid(row=13,column=1)
        #Create button to add wis Value
        add_wis_btn = customtkinter.CTkButton(master=self.frame_left, text="Add WIS Value", command=add_wis)
        add_wis_btn.grid(row=13, column=2)

        #CHA Combobox
        cha_label = customtkinter.CTkLabel(master=self.frame_left, text="CHA Option")
        cha_label.grid(row=14,column=0)
        cha_combobox = customtkinter.CTkComboBox(master=self.frame_left, values=stats_options_combobox)
        cha_combobox.grid(row=14, column=1)
        cha_combobox.set("Random")
        current_cha = cha_combobox.current_value
        #Add cha Value function
        def add_cha():
            cha_choice = StringVar()
            cha_choice = cha_combobox.get()
            random_cha = random.choice(stats_options_label)
            if cha_choice == "Random":
                display_cha['text'] = random_cha
            else:
                display_cha['text'] = cha_choice
        #Display cha Value
        display_cha = customtkinter.CTkLabel(master=self.frame_right, text='')
        display_cha.grid(row=14,column=1)
        #Create button to add cha Value
        add_cha_btn = customtkinter.CTkButton(master=self.frame_left, text="Add CHA Value", command=add_cha)
        add_cha_btn.grid(row=14, column=2)

        #--------- Saving Throws ---------#
        #TODO Create IF statement for Saves based on stats
        
        # ----------- Skills ------------#
        #Skills combobox
        skills_label = customtkinter.CTkLabel(master=self.frame_left, text="Skills Option")
        skills_label.grid(row=15,column=0)
        skills_options_combobox = ["Random","Acrobatics","Animal Handling",
                        "Arcana","Athletics","Deception",
                        "History","Insight","Intimidation",
                        "Investigation","Medicine","Nature",
                        "Perception","Performance","Persuasion",
                        "Religion","Sleight of Hand","Stealth",
                        "Survival",
                        ]
        skills_options_label = ["Random","Acrobatics","Animal Handling",
                        "Arcana","Athletics","Deception",
                        "History","Insight","Intimidation",
                        "Investigation","Medicine","Nature",
                        "Perception","Performance","Persuasion",
                        "Religion","Sleight of Hand","Stealth",
                        "Survival",
                        ]
        skills_combobox = customtkinter.CTkComboBox(master=self.frame_left, values=skills_options_combobox)
        skills_combobox.grid(row=15, column=1)
        skills_combobox.set("Random")
        current_skills = skills_combobox.current_value
        #Skills value combobox
        skills_value_options_combobox = ["Random","+1","+2","+3",
                                    "+4","+5","+6","+7","+8",
                                    "+9","+10"]
        skills_value_options_label = ["+1","+2","+3",
                                    "+4","+5","+6","+7","+8",
                                    "+9","+10"]
        skills_value_combobox = customtkinter.CTkComboBox(master=self.frame_left, values=skills_value_options_combobox)
        skills_value_combobox.grid(row=15, column=2)
        skills_value_combobox.set("Random")
        current_skills_value = skills_value_combobox.current_value
        #Create list of Skills
        skills_list = []    

        #Add Skills function
        def add_skills():
            #Type
            skills_choice = StringVar()
            skills_choice = skills_combobox.get()
            random_skills = random.choice(skills_options_label)
            #Value
            skills_value_choice = StringVar()
            skills_value_choice = skills_value_combobox.get()
            random_skills_value = random.choice(skills_value_options_label)
            
            if any(skills_choice in s for s in skills_list):
                tkinter.messagebox.showinfo('Error', f'{skills_choice} Skill already added.')
            else:                                    
                if skills_choice == "Random" and skills_value_choice == "Random":
                    skills_list.append(random_skills + ' ' + random_skills_value)
                    display_skills['text'] = ' | '.join(skills_list)
                                                
                elif skills_choice == "Random" and skills_value_choice != "Random":
                    skills_list.append(random_skills + ' ' + skills_value_choice)
                    display_skills['text'] = ' | '.join(skills_list)

                elif skills_choice !="Random" and skills_value_choice == "Random":
                    skills_list.append(skills_choice + ' ' + random_skills_value)
                    display_skills['text'] = ' | '.join(skills_list)

                elif skills_choice !="Random" and skills_value_choice != "Random":
                    skills_list.append(skills_choice + ' ' + skills_value_choice)
                    display_skills['text'] = ' | '.join(skills_list)
            
        #Display Skills
        display_skills = customtkinter.CTkLabel(master=self.frame_right, text='')
        display_skills.grid(row=15,column=1)
        #Create button to add Skills
        add_skills_btn = customtkinter.CTkButton(master=self.frame_left, text="Add Skills",command=add_skills)
        add_skills_btn.grid(row=15, column=3)


        # ------------- Vulnerabilites ----------#
        #Vulnerabilites combobox
        vuln_label = customtkinter.CTkLabel(master=self.frame_left, text="Vulnerability Option")
        vuln_label.grid(row=16,column=0)
        vuln_options_combobox = ["Random","Acid","Cold","Fire",
                        "Force","Lightning","Necrotic",
                        "Poison","Psychic","Radiant",
                        "Thunder","Bludgeoning","Slashing",
                        "Piercing","Magical","Magical Bludgeoning",
                        "Magical Slashing","Magical Piercing",
                        ]
        vuln_options_label = ["Random","Acid","Cold","Fire",
                        "Force","Lightning","Necrotic",
                        "Poison","Psychic","Radiant",
                        "Thunder","Bludgeoning","Slashing",
                        "Piercing","Magical","Magical Bludgeoning",
                        "Magical Slashing","Magical Piercing",
                        ]
        vuln_combobox = customtkinter.CTkComboBox(master=self.frame_left, values=vuln_options_combobox)
        vuln_combobox.grid(row=16, column=1)
        vuln_combobox.set("Random")
        current_vuln = vuln_combobox.current_value
        #Create Vuln list
        vuln_list = []
        #Add vuln Value function
        def add_vuln():
            vuln_choice = StringVar()
            vuln_choice = vuln_combobox.get()
            random_vuln = random.choice(vuln_options_label)
            if vuln_choice in vuln_list:
                tkinter.messagebox.showinfo('Error', f'{vuln_choice} Vulneability already added.')
            else:
                if vuln_choice == "Random":
                    vuln_list.append(random_vuln)
                    display_vuln['text'] = ' | '.join(vuln_list)
                else:
                    vuln_list.append(vuln_choice)
                    display_vuln['text'] = ' | '.join(vuln_list)
                
        #Display vuln Value
        display_vuln = customtkinter.CTkLabel(master=self.frame_right, text='')
        display_vuln.grid(row=16,column=1)
        #Create button to add vuln Value
        add_vuln_btn = customtkinter.CTkButton(master=self.frame_left, text="Add Vulnerability", command=add_vuln)
        add_vuln_btn.grid(row=16, column=2)
        

                            # ------------ Immunities ---------#
        #Immunities combobox
        immune_label = customtkinter.CTkLabel(master=self.frame_left, text="Immunity Option")
        immune_label.grid(row=17,column=0)
        immune_options_combobox = ["Random","Acid","Cold","Fire",
                        "Force","Lightning","Necrotic",
                        "Poison","Psychic","Radiant",
                        "Thunder","Bludgeoning","Slashing",
                        "Piercing","Magical","Magical Bludgeoning",
                        "Magical Slashing","Magical Piercing",
                        ]
        immune_options_label = ["Acid","Cold","Fire",
                        "Force","Lightning","Necrotic",
                        "Poison","Psychic","Radiant",
                        "Thunder","Bludgeoning","Slashing",
                        "Piercing","Magical","Magical Bludgeoning",
                        "Magical Slashing","Magical Piercing",
                        ]
        immune_combobox = customtkinter.CTkComboBox(master=self.frame_left, values=immune_options_combobox)
        immune_combobox.grid(row=17, column=1)
        immune_combobox.set("Random")
        current_immune = immune_combobox.current_value
        #Add list of immunes
        immune_list = []
        #Add immune Value function
        def add_immune():
            immune_choice = StringVar()
            immune_choice = immune_combobox.get()
            random_immune = random.choice(immune_options_label)
            if immune_choice in immune_list:
                tkinter.messagebox.showinfo('Error', f'{immune_choice} Immunity already added.')
            else:
                if immune_choice == "Random":
                    immune_list.append(random_immune)
                    display_immune['text'] = ' | '.join(immune_list)
                else:
                    immune_list.append(immune_choice)
                    display_immune['text'] = ' | '.join(immune_list)
                
        #Display immune Value
        display_immune = customtkinter.CTkLabel(master=self.frame_right, text='')
        display_immune.grid(row=17,column=1)
        #Create button to add immune Value
        add_immune_btn = customtkinter.CTkButton(master=self.frame_left, text="Add Immunity", command=add_immune)
        add_immune_btn.grid(row=17, column=2)

        # ---------- Resistances -----------#
        #Resistances combobox
        resist_label = customtkinter.CTkLabel(master=self.frame_left, text="Resistance Option")
        resist_label.grid(row=18,column=0)
        resist_options_combobox = ["Random","Acid","Cold","Fire",
                        "Force","Lightning","Necrotic",
                        "Poison","Psychic","Radiant",
                        "Thunder","Bludgeoning","Slashing",
                        "Piercing","Magical","Magical Bludgeoning",
                        "Magical Slashing","Magical Piercing",
                        ]
        resist_options_label = ["Acid","Cold","Fire",
                        "Force","Lightning","Necrotic",
                        "Poison","Psychic","Radiant",
                        "Thunder","Bludgeoning","Slashing",
                        "Piercing","Magical","Magical Bludgeoning",
                        "Magical Slashing","Magical Piercing",
                        ]
        resist_combobox = customtkinter.CTkComboBox(master=self.frame_left, values=resist_options_combobox)
        resist_combobox.grid(row=18, column=1)
        resist_combobox.set("Random")
        current_resist = resist_combobox.current_value
        #Resistance Add button
        resist_add_button = customtkinter.CTkButton(master=self.frame_left, text="Add Resistance")
        resist_add_button.grid(row=18,column=2)
        #Create resist list
        resist_list = []
        #Add resist Value function
        def add_resist():
            resist_choice = StringVar()
            resist_choice = resist_combobox.get()
            random_resist = random.choice(resist_options_label)
            if resist_choice in resist_list:
                tkinter.messagebox.showinfo('Error', f'{resist_choice} Resistance already added.')
            else:
                if resist_choice == "Random":
                    resist_list.append(random_resist)
                    display_resist['text'] = ' | '.join(resist_list)
                else:
                    resist_list.append(resist_choice)
                    display_resist['text'] = ' | '.join(resist_list)
                
        #Display resist
        display_resist = customtkinter.CTkLabel(master=self.frame_right, text='')
        display_resist.grid(row=18,column=1)
        #Create button to add resist
        add_resist_btn = customtkinter.CTkButton(master=self.frame_left, text="Add Resistance", command=add_resist)
        add_resist_btn.grid(row=18, column=2)

        # -------- Senses ---------#
        #Sense combobox
        senses_label = customtkinter.CTkLabel(master=self.frame_left, text="Senses Option")
        senses_label.grid(row=19,column=0)
        senses_options_combobox = ["Random","Darkvision","Blindsight","Truesight","Tremorsense"]
        senses_options_label = ["Random","Darkvision","Blindsight","Truesight","Tremorsense"]
        senses_combobox = customtkinter.CTkComboBox(master=self.frame_left, values=senses_options_combobox)
        senses_combobox.grid(row=19, column=1)
        senses_combobox.set("Random")
        current_sense = senses_combobox.current_value
        #Sense value combobox
        senses_value_options_combobox = ["Random",
                                "10 ft","20 ft","30 ft",
                                "40 ft","50 ft","60 ft",
                                "70 ft","80 ft","90 ft",
                                "100 ft","110 ft","120 ft"
                                ]
        senses_value_options_label = [
                                "10 ft","20 ft","30 ft",
                                "40 ft","50 ft","60 ft",
                                "70 ft","80 ft","90 ft",
                                "100 ft","110 ft","120 ft"
                                ]
        senses_value_combobox = customtkinter.CTkComboBox(master=self.frame_left, values=senses_value_options_combobox)
        senses_value_combobox.grid(row=19, column=2)
        senses_value_combobox.set("Random")
        current_sense_value = senses_value_combobox.current_value
        #Create list of senses
        senses_list = []    

        #Add senses function
        def add_senses():
            #Type
            senses_choice = StringVar()
            senses_choice = senses_combobox.get()
            random_senses = random.choice(senses_options_label)
            #Value
            senses_value_choice = StringVar()
            senses_value_choice = senses_value_combobox.get()
            random_senses_value = random.choice(senses_value_options_label)
            
            if any(senses_choice in s for s in senses_list):
                tkinter.messagebox.showinfo('Error', f'{senses_choice} Sense already added.')
            else:                                    
                if senses_choice == "Random" and senses_value_choice == "Random":
                    senses_list.append(random_senses + ' ' + random_senses_value)
                    display_senses['text'] = ' | '.join(senses_list)
                                                
                elif senses_choice == "Random" and senses_value_choice != "Random":
                    senses_list.append(random_senses + ' ' + senses_value_choice)
                    display_senses['text'] = ' | '.join(senses_list)

                elif senses_choice !="Random" and senses_value_choice == "Random":
                    senses_list.append(senses_choice + ' ' + random_senses_value)
                    display_senses['text'] = ' | '.join(senses_list)

                elif senses_choice !="Random" and senses_value_choice != "Random":
                    senses_list.append(senses_choice + ' ' + senses_value_choice)
                    display_senses['text'] = ' | '.join(senses_list)
            
        #Display senses
        display_senses = customtkinter.CTkLabel(master=self.frame_right, text='')
        display_senses.grid(row=19,column=1)
        #Create button to add senses
        add_senses_btn = customtkinter.CTkButton(master=self.frame_left, text="Add Senses",command=add_senses)
        add_senses_btn.grid(row=19, column=3)

        #---------- Languages ----------#
        #Languages combobox
        lang_label = customtkinter.CTkLabel(master=self.frame_left, text="Languages Option")
        lang_label.grid(row=20,column=0)
        lang_options_combobox = ["Random","Common","Dwarvish",
                        "Elvish","Giant","Gnomish",
                        "Goblin","Halfling","Orc",
                        "Abyssal","Celestial","Deep Speech",
                        "Draconic","Infernal","Primordial",
                        "Sylvan","Undercommon"
                        ]
        lang_options_label = ["Random","Common","Dwarvish",
                        "Elvish","Giant","Gnomish",
                        "Goblin","Halfling","Orc",
                        "Abyssal","Celestial","Deep Speech",
                        "Draconic","Infernal","Primordial",
                        "Sylvan","Undercommon"
                        ]
        lang_combobox = customtkinter.CTkComboBox(master=self.frame_left, values=lang_options_combobox)
        lang_combobox.grid(row=20, column=1)
        lang_combobox.set("Random")
        current_lang = lang_combobox.current_value
        #Language Add button
        lang_add_button = customtkinter.CTkButton(master=self.frame_left, text="Add Language")
        lang_add_button.grid(row=20,column=2)
        #Create lang list
        lang_list = []
        #Add lang Value function
        def add_lang():
            lang_choice = StringVar()
            lang_choice = lang_combobox.get()
            random_lang = random.choice(lang_options_label)
            if lang_choice in lang_list:
                tkinter.messagebox.showinfo('Error', f'{lang_choice} Language already added.')
            else:
                if lang_choice == "Random":
                    lang_list.append(random_lang)
                    display_lang['text'] = ' | '.join(lang_list)
                else:
                    lang_list.append(lang_choice)
                    display_lang['text'] = ' | '.join(lang_list)
                
        #Display lang
        display_lang = customtkinter.CTkLabel(master=self.frame_right, text='')
        display_lang.grid(row=20,column=1)
        #Create button to add lang
        add_lang_btn = customtkinter.CTkButton(master=self.frame_left, text="Add Language", command=add_lang)
        add_lang_btn.grid(row=20, column=2)


        ###TODO
        #Special traits value combobox
        special_traits_label = customtkinter.CTkLabel(master=self.frame_left, text="Special Traits Option")
        special_traits_label.grid(row=21,column=0)
        special_traits_options = ["Random"]
        special_traits_combobox = customtkinter.CTkComboBox(master=self.frame_left, values=special_traits_options)
        special_traits_combobox.grid(row=21, column=1)
        special_traits_combobox.set("Random")
        current_special_traits = special_traits_combobox.current_value
        #Language Add button
        special_traits_add_button = customtkinter.CTkButton(master=self.frame_left, text="Add Special Trait")
        special_traits_add_button.grid(row=21,column=2)

        ###TODO
        #Actions value combobox
        actions_label = customtkinter.CTkLabel(master=self.frame_left, text="Actions Option")
        actions_label.grid(row=22,column=0)
        actions_options = ["Random"]
        actions_combobox = customtkinter.CTkComboBox(master=self.frame_left, values=actions_options)
        actions_combobox.grid(row=22, column=1)
        actions_combobox.set("Random")
        current_actions = actions_combobox.current_value
        #Actions Add button
        actions_add_button = customtkinter.CTkButton(master=self.frame_left, text="Add Action")
        actions_add_button.grid(row=22,column=2)

        ###TODO
        #Legendary Actions value combobox
        legendary_actions_label = customtkinter.CTkLabel(master=self.frame_left, text="Legendary Actions Option")
        legendary_actions_label.grid(row=23,column=0)
        legendary_actions_options = ["Random"]
        legendary_actions_combobox = customtkinter.CTkComboBox(master=self.frame_left, values=legendary_actions_options)
        legendary_actions_combobox.grid(row=23, column=1)
        legendary_actions_combobox.set("Random")
        current_legendary_actions = legendary_actions_combobox.current_value
        #Legendary Actions Add button
        legendary_actions_add_button = customtkinter.CTkButton(master=self.frame_left, text="Add Legendary Action")
        legendary_actions_add_button.grid(row=23,column=2)

        ###TODO
        #Lair Actions value combobox
        lair_actions_label = customtkinter.CTkLabel(master=self.frame_left, text="Lair Actions Option")
        lair_actions_label.grid(row=24,column=0)
        lair_actions_options = ["Random"]
        lair_actions_combobox = customtkinter.CTkComboBox(master=self.frame_left, values=lair_actions_options)
        lair_actions_combobox.grid(row=24, column=1)
        lair_actions_combobox.set("Random")
        current_lair_actions = lair_actions_combobox.current_value
        #Lair Actions Add button
        lair_actions_add_button = customtkinter.CTkButton(master=self.frame_left, text="Add Lair Action")
        lair_actions_add_button.grid(row=24,column=2)

        ###TODO
        #Spells value combobox
        spells_label = customtkinter.CTkLabel(master=self.frame_left, text="Spells Option")
        spells_label.grid(row=25,column=0)
        spells_options = ["Random"]
        spells_combobox = customtkinter.CTkComboBox(master=self.frame_left, values=spells_options)
        spells_combobox.grid(row=25, column=1)
        spells_combobox.set("Random")
        current_spells = spells_combobox.current_value
        #Spell Add button
        spell_add_button = customtkinter.CTkButton(master=self.frame_left, text="Add Spell")
        spell_add_button.grid(row=25,column=2)

        #TODO Export to PDF 
        #------ Display Stats ----#
        
        for index, row in enumerate(self.monster_stat_list): 
            monster_stats_label = customtkinter.CTkLabel(master=self.frame_right, 
                                                        text=row + ":")
                                                        
            #may want to add index + 1 to start it on row 2 
            monster_stats_label.grid(row=index, column=0,padx=1,pady=1, sticky="w")

        #TODO
        #------Remove Button------#
        def remove_stat():
            # Toplevel object which will
            # be treated as a new window
            remove_stat_window = customtkinter.CTkToplevel(master)
        
            # sets the title of the
            # Toplevel widget
            remove_stat_window.title("Remove Stat")
        
            # sets the geometry of toplevel
            remove_stat_window.geometry("400x400")
        
            # A Label widget to show in toplevel
            Label(remove_stat_window,
                text ="This is a new window").pack()

        remove_btn = customtkinter.CTkButton(master=self.frame_left, text="Remove Stat?", command=remove_stat)
        remove_btn.grid(row=28,column=0, columnspan=4)

        #TODO
        #------------Save Monster------------#
        # def save_monster():
        #     file = open("monster.txt", "w")
        #     file.write("Monster Name: " + monster_name + 
        #                 "\n" + "Size: "+ display_size.cget("Text"))
        #     file.close 
        # save_btn = customtkinter.CTkButton(master=self.frame_left,text="Save to File", command=save_monster)
        # save_btn.grid(row=29,column=0, columnspan=4)
              


if __name__ == "__main__":
    app = App()
    app.mainloop()

Answer 1

The biggest "yikes" about this is your __init__. Having a nearly 1,000-line method under any circumstances is a big giveaway that refactoring is needed. Pull out your widget creation into multiple methods grouped by theme or functionality. Pull out most or all of your nested functions (generate_monster, etc.) into regular class methods.

Use an IDE (Pycharm or other) that gives you sane linting and listen to its recommendations. Lots of unused cruft that needs to be deleted, e.g. current_monster_type.

The user interface itself is very impressive! On my machine it currently looks like

I think the division between the left and right pane is awkward. Consider instead a single-table layout with an example row looking like

Size, Random dropdown, Add, and then a read-only label that only reads Tiny once generated.

In other words, don't write Size three times (label, button, label); only write it once. You could even contract "Add" to a single + symbol for brevity. And delete "Option" everywhere.