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.