We do split stays a lot. A few random thoughts:
1. The hardest part of the split stay is the packing/unpacking for us, so you should try to think of ways to make it easy for yourself. Pack your stuff in the same way it is stored. Bring a few extra thin bags if necessary. That is, everything on the bathroom goes together. All the clothes in one drawer goes into the same bag. That way, you put everything into a bags quickly, and when you get into the new room, take everything out and put them in the (relatively) the same area quickly. Everything will then be easy to find, like you never moved.
2. Disney can be very slow at delivering bags to your room. Once they brought my bag to me at 9:30 at night even though I gave it to them at 9 in the morning. I even tried to go get it myself at bell service around 6, but they said somebody was gone delivering it. Took the guy more than 3 hours to get to mine. That was All Star Music.
3. Disney told me that to have them transfer your bags, you must get the bags in by 11am and it will be at the new hotel by 4 p.m. The best way is to call them around 3 pm to check if they have it. We transfer to the Grand Floridian once. By 5 we still didn't have our luggage, so I called them and asked if our bags are there? They said Oh yes! I said can you deliver it? They said Oh, sure! And the bell boy showed up in 5 minutes. Have they been waiting for me to call?
4. If you decide to haul your own luggage by taxi, give it to the bell boy and tell them to store it, you will come to get it later. That way, you don't get stuck with your luggage being stuck on the bell boy's delivery cart for 3 hours.
5. No, I disagree with the going "low to high" plan. I think the most important point is the weekends and money. That is, let's say your plan is Pop, POR, AKL. Then AKL should be done during the middle of the week and Pop on the weekends, with POR in between. The reason is, AKL will cost much more for the weekend than the week. Pop will also be more expensive, but not near as much. And I don't believe you will look at Pop with disdain after having been at AKL. It is beautiful in its own way. Just last month, we moved from Beach Club back to Pop. We did not appreciate it one bit less. I only did Beach Club so that the kids could use the pool. I adore Pop! It's like visiting Epcot one day and then Hollywood studios the next. It's not worse, it's just different.
5.On your checkout day, if your magic band quits working for the pool etc, don't be shy to ask them to fix it. We checked out of Polynesian Club level one day and all our magic bands stopped working for the pool at 1 p.m. We went back in to make them reactivate it, and they did. It was really annoying, though.
6. Stay in your room until 11am, if possible, then leave to do the pool and lunch and transfer. By the time that's all done, it will be at least 3 p.m.
7. Don't wait for the room text. Once you arrive at the next hotel, if you haven't gotten the text, go to the front desk to check to see if the room is ready. I often don't get the text, and the room is ready before 3 p.m. That's if you need the room right away, of course. And double check your settings in your
MDE account to make sure the correct cell number is in there.
8. Be sure that you get the DME letter to board the airport bus the day before your departure.
9. If you are not taking the taxi/uber, you can go from hotel to hotel using parks as transfer points. That does take quite a bit longer, but that's good if you got time to kill, and you will be traveling mid day so that buses won't be crowded.
10. Find out if the hotel has a comfortable spot that your family can rest in case the pool is closed due to weather. My kids like to visit the video game arcades at Pop if we need to kill time.
Transfer days can seem like you are out of a room, but you won't notice it if you plan it right.