We have done this once before. I would say start with the value and then go to the deluxe next that way you are moving up and not down . Also Disney makes it pretty easy, they will transport your luggage for you! Something we did to make our life easier on our last vacation (as read on the disboards!) was to use a hanging shoe rack on the back of the door for all of our stuff. Everyone had a few pouches and it kept everything super organized and off the sink. It also made it super easy to move and unpack at the next stop! Just roll it up and then get it back out!!!