Yes, you have to make two separate reservations. Yes Disney will move your luggage, you just call bell services either the night before or morning of and they will come get the bags and send them to the 2nd resort. They do not guarantee they will be there before 3. I do a lot of split stays and I've found if you actually check out of resort #1 before leaving it will go smoother. I just call the front desk on the phone before I leave the room. Even though I do on line check in, I always go to the front desk of resort #2 to just let them know I'm there in case a room can be ready early. It's not necessary though, if you do on line check in you will get the text when your room is ready. I drive down so I call and check out of resort #1 around 7:30 just because I'm up then, drive over to resort #2 and either leave my bags in my car and go check in or drop my bags off with BS and park then go check in. If my rooms ready, rarely, I go ahead and go up then off to a park, if it's not ready I just go off to a park and when I get the text the room is ready if I'm ready to go back, I do, otherwise I go back whenever I'm ready. I don't know about if you transfer your bags from another resort but if you leave your bags with BS because your room isn't ready, you have to be in your room and call down before they will bring them up, they will not deliver them to the room without you being there. They might do it if you transfer them though.
