It all depends on the length of your stay. I prefer not to split my stays if I'm there for less than 5 nights. In Dec, I spend my first night at AoA (LM room!!!), then five nights at SSR, and my last night with a friend at BWV. I'm traveling solo, so I have only myself to pack for.
there was the one trip, about 2 years ago, that I moved constantly....1 night at Jambo House, then 4 nights at BWV, then my travel buddy went home and I met up with another friend and moved to Kidani for 2 nights with her. Then, 5 nights at Pop for
free dining, and finally back to BWV for my last 2 nights. I was always having to stop and remember exactly which bus to get on to get back to my resort!!
But since I've done it so many times, it's no big deal anymore. Just pack up as much as you can the night before you move. Leave out only what you really need for the morning. Then, as soon as you're ready, call and get your bags collected and sent along to the next resort. Then, you can head to a park for a few hours and then take the bus to the next resort and get checked in. You won't get your luggage until about 5pm, so plan accordingly.
If it's important to have your bags with you, take a cab, with your bags, to the next resort. It's quicker and you can have access to your bags.