We tried a split stay for the first time last Christmas, and now we are HOOKED! We've been back and done another split stay in Feb/March of this year, and what works for us is to plan our schedule and hotel around the parks we want to visit those days. So for us that has meant planning MK & AK days (we take a Minnie van to AK) for nights we're staying at a MK hotel, then about midway through the trip we'll switch to an EP hotel and visit EP and HS those days. We really like being able to walk/boat/monorail to the hotels rather than rely on buses, so this has worked well for us.
The other thing that helps make the packing/unpacking issue less of a hassle is to use packing cubes. We pack one or two cubes for each hotel, then we write the hotel name on the front of an index card, and on the back we list every item packed in that cube, and then place the index card just under the meshy area of the packing cube so we can still read it. That way, we only have to take out that one (or two) cube(s) at each hotel, and the other stays put away in the suitcase -- plus you have an inventory in case something goes missing (happens at least once a trip for us lol). Dirty clothes are placed in a trash bag we bring from home until it's time to pack up, and then we just put them back in their designated cube. Everyone in my family has toiletry bags (I have several for all my gear, lol), so they're easy to keep everything organized and either just put in the bathroom vanity or throw in our suitcase/carry on. I learned the packing cube tip from someone here on this Disboards -- apologies that I don't remember who it was, because it was a game changer for us.
We also tend to pack very light for trips...I am 5'0" and H is 6'6" so it's incredibly difficult to find clothes that fit. One incident years ago of the airline losing our luggage taught me to never check bags, so we each only bring a 22" roller bag and a smaller tote style bag or backpack. Admittedly a split stay would be more difficult if you're not a light packer or have a young child with lots of gear to bring, but I think it's still possible as long as you're organized and have a plan.
As others have mentioned, we bring our bags out to bell services the morning we switch hotels and have them delivered for us. We typically plan for this to be an AK day, as we tend to plan long, all-day park days when we're there since transportation is the most time consuming from most hotels we typically stay at. We've always been lucky enough to have our bags waiting for us when we've gotten to our new hotel in the evening.
HTH!
