For those that DON"T like split stays...

Honestly I think the split stay will be fine. As long as you understand you might be out of a room in between, it's really not too bad. Personally I do find them a tad bit annoying when it comes to packing stuff up to switch rooms, but the benefits of them outweigh the negatives, especially in this case. WL and YC are my two favorites on property and they both provide unique experiences and benefits. WL is great for MK access while not being as pricey as monorail resorts, and YC is amazing for HS and Epcot for sure, but the boardwalk area can't be beat. At Christmas, both resorts are beautifully decorated and offer convenience that is unique to their areas. I'd say just make some plans to kill the time it might take in between getting your new rooms (i.e. going to the park, a sit down lunch, Disney springs, etc.), and don't really rush yourself when it comes to checking out and moving to your next room.
 
We have done it many times including during Christmas/New years weeks pretty much for the same reasons you are! We typically spend NYE at Epcot and the only way this works for us is to be at an Epcot resort so we usually start out at a moderate and then splurge for a couple nights around NYE.

As long as you plan for not having a room until at least 4 your fine. Most times we bring our bags to bell services to transfer and head out for the day, since we rarely return to the new resort before 6 ish our room is always ready and our bags have always been at bell services. Last trip we didn't have firm plans for the day so we took a Lyft from Poly to YC around 11am with our bags since it was a hot day and we were thinking of heading to the pool if our room was ready. Turned out that our room wasn't ready so we just checked our bags with bell services and headed to the studios instead.

The packing aspect/hassle is different for everyone - I unpack only what I need for each stay and then repack accordingly. My kids live out of the suitcase so they are pretty much ready to go at all times LOL.
 
The un-packing and re-packing is what I find hard about a split stay. I try my best to organize things so that only certain bags/packing cubes need to be opened at each location. That way I'm not unpacking and repacking everything...because Ugh! ;)
 
Awesome feed back. Thanks so much. I hadn’t thought about the Minnie van for the transfer. That is a good idea.
 













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