You would have to do it for 2 packages. Luckily with the new MYW packages you can pick the tickets you need so no issue there, but as far as the dining plan you will be paying for one day twice. The way it is divided up you would get credits for the first stay (good until midnight on check out day) and then credits for the next stay (good starting when you check in). You would have to pay for the extra credits, but you would not be wasting money as long as you use them all. It still might be a money saver if you like TS meals.