We are dedicated resort-hoppers. It doesn't seem like Disney unless we move at least once!
For us, it's pretty easy. Here are a few tips.
1) Hop "Up"; stay at a less-expensive (or your second favorite) place first, leaving yourself a special treat to look forward to after you've seen the parks and can enjoy it a bit more.
2) Get Express Checkout. When you check in to your first resort, let them know you want express checkout. They'll hang a copy of your bill on your door the morning you check out, you just look it over and leave.
3) Use Bell Services. Call them the night before you move to find out how it works at your resort. Sometimes they will schedule a time to pick up and move your bags right then, sometimes they'll recommed you call back in the morning. Get up in the morning, send your bags on their way, and head to the parks.
4) Keep a bag of swimsuits and essentials. Bring it to the parks and put it in a locker (or leave it in your trunk). That way if resort #2 doesn't have a room ready for you yet, you can swim and enjoy the amenities until it is.
5) Check in to resort 2 when they're not busy. Sometimes the lines to check in can be LOOOONG. We often call the desk to find out when they are usually least busy, so we can avoid the lines if possible. (usually early afternoon).
6) Check in when it's convenient for you. Your room might be available early (we've gotten in as early as 8AM). If your room isn't ready yet, they'll issue you keys and give you a number to call to check if it's ready. Then you can enjoy the resort, have lunch, or head back to the parks. Your bags will either be in your room when you arrive, or a quick call to bell services will have them there shortly.
As I said, I really recommend resort-hopping. Our last trip took us to 4 resorts, and we really enjoyed the change of scenery; we stayed at ASMu the first 6 nights, then moved on to WL and AKL concierge when we could spend time at them and enjoy them!
(Yes, it does take separate ressies and deposits, you can make them both at the same time...)