I would suggest if you do decide to do it, to get up early and go ahead to your next resort and actually check in at the front desk. As others have mentioned, there can be problems with magic bands. I've never had to actually check out of resort #1 because I do the express check out thing, but I always go to resort #2 very early and check in. I'm an early riser so it is no problem for me, I do normally do the on line check in and say I'm getting there early, I've found when I do that there is a better chance a room will be ready. I still go to the front desk, just to check my magic band and because it makes me feel better. Because I drive it's easier to go ahead and move my car to the resort #2 early in the morning as well, that way I don't feel like a little lost orphan. Also, if you don't want to use different bags, you can either use packing cubes or good ole fashioned big ole zip lock bags, pack your outfits for separate days in each bag, roll that puppy getting all the air out and zip it, then all you have to do is rotate out the bags and they pack a whole lot easier since they are smaller. If you don't want to do each days outfit that way, possibly all the shorts for one part of the trip in one bag, all the shirts for one part in another, etc. Again then you just have to pull that trips bags out of the big bag and when you are done with them, those dirty clothes go back into the zip lock and get rotated to the bottom of the bag.