My script doesn't work multiple times?

I think you forgot to set the debounce to true again? I mean, line 09 sets the debounce to false and no other lines seem to put it back to true?

Try this I guess.

CurrentPrice = script.Parent.Worth
	Debounce = true
	PickedUp = false
	 
	 
	script.Parent.Touched:Connect(function(hit)
	    if Debounce and hit.Parent.Parent:FindFirstChild("Humanoid") and hit.Parent.Name == "Trashpick" and not PickedUp then
	        print("Trash is now PickedUp")     
	        Debounce = false
	        script.Parent.Transparency = 1
	        local player = game.Players:GetPlayerFromCharacter(hit.Parent.Parent)
 
	        player:FindFirstChild("leaderstats")
	        player.leaderstats.Cash.Value = player.leaderstats.Cash.Value + CurrentPrice.Value
	        print("Player picked up trash")
	 
	        PickedUp = true
	        wait(10)
	        PickedUp = false
		Debounce = true -- Resets variable Debounce back to true
	        script.Parent.Transparency = 0
	 
	    end
	 
	    end)

Just a little mistake if I am right.