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.