ResponseDialog won't change based on global variables?

So, I'm trying to write a script that will assign different strings in the ResponseDialog of five DialogChoices, based on the player's TeamColor and the "Cash" value in their Cash Gui. Currently, the script works as planned in Edit > Play, but when I do a server test, the DialogChoices give the default ResponseDialog, rather than what the script assigns to them. I've tried monitoring the ResponseDialog of the DialogChoice while doing a server test, and I've found that the ResponseDialog changes to the desired string AFTER the DialogChoice gives the ResponseDialog. I've looked on the Roblox Wiki and I've checked with similar forum posts, but nothing seems to help. Does anyone know how to fix this?

Here's the current script:

for _,v in pairs (game.ReplicatedStorage.Weapons:GetChildren()) do
	weps = v.Name
	print("Guns Script: "..weps)
end
Weapons = game.ReplicatedStorage.Weapons



local dialog1 = script.Parent
dialog1.DialogChoiceSelected:connect(function(player, choice)
		if player.TeamColor == BrickColor.new("Black") then
			script.Parent.Gun.ResponseDialog = "You came to the right place. How can I be of assistance?"
			for _,i in pairs (dialog1.Choices:GetChildren()) do
				i:Clone()
				i.Parent = dialog1.Gun
			end
			
			if choice.Name == "Choice1" then
				local dialog2 = script.Parent.Gun
				
				if player.PlayerGui.Cash.Cash.Value >= 500 then
					print("Player Money: "..player.PlayerGui.Cash.Cash.Value)
					dialog2.Choice1.ResponseDialog = "Sure, pal. Thanks for the business."
					
					local pistol = Weapons.pistol:Clone()
					pistol.Parent = player.Backpack
					pistol.Name = "Concealed Firearm"
					player.PlayerGui.Cash.Cash.Value = (player.PlayerGui.Cash.Cash.Value - 500)
				else
					dialog2.Choice1.ResponseDialog = "Not unless you have $500."
				end
			end
			
			if choice.Name == "Choice2" then
				local dialog3 = script.Parent.Gun
			
				if player.PlayerGui.Cash.Cash.Value >= 5000 then
					print("Player Money: "..player.PlayerGui.Cash.Cash.Value)
					dialog3.Choice2.ResponseDialog = "Alright. Try this on for size."
					
					local smg = Weapons.smg:Clone()
					smg.Parent = player.Backpack
					smg.Name = "MP5K"
					player.PlayerGui.Cash.Cash.Value = (player.PlayerGui.Cash.Cash.Value - 5000)
				else
					dialog3.Choice2.ResponseDialog = "Sure thing. Find $5000, and get back to me."
				end
			end
			
			if choice.Name == "Choice3" then
				local dialog3 = script.Parent.Gun
			
				if player.PlayerGui.Cash.Cash.Value >= 100 then
					print("Player Money: "..player.PlayerGui.Cash.Cash.Value)
					dialog3.Choice3.ResponseDialog = "How about one of my signature switchblades?"
					
					local knife = Weapons.knife:Clone()
					knife.Parent = player.Backpack
					knife.Name = "Switch    Blade"
					player.PlayerGui.Cash.Cash.Value = (player.PlayerGui.Cash.Cash.Value - 100)
				else
					dialog3.Choice3.ResponseDialog = "If you can get your hands on $100, then yes."
				end
			end
			
			if choice.Name == "Choice4" then
				local dialog4 = script.Parent.Gun
			
				if player.PlayerGui.Cash.Cash.Value >= 200 then
					print("Player Money: "..player.PlayerGui.Cash.Cash.Value)
					dialog4.Choice4.ResponseDialog = "Here you go. Don't get too cocky, though - I'm not a very good artist."
					
					local badge = Weapons.badge:Clone()
					badge.Parent = player.Backpack
					badge.Name = "Counterfeit ID Badge"
					player.PlayerGui.Cash.Cash.Value = (player.PlayerGui.Cash.Cash.Value - 200)
				else
					dialog4.Choice4.ResponseDialog = "Get $200, then I'll be happy to help you."
				end
			end
		else
			script.Parent.Gun.ResponseDialog = "As a matter of fact, I'm not. Now get outta my face."
			for _,v in pairs (dialog1.Gun:GetChildren()) do
                        if v ~= nil then
				print(v)
				v:Destroy()
                        end
			end
		end
end)

If it helps, here's the hierarchy of the Dialog, the Weapons, and the Cash Gui, with the above script highlighted in red:

http://prntscr.com/7jl4cb http://prntscr.com/7jl4e8 http://prntscr.com/7jl4fz

If need be, I'd be happy to lend anyone the objects listed above if it helps them understand the script or find a solution.