We have done split resorts trips in the past, but not since having kids.
Actually I am wrong. DVC points is more on the weekend so a few times we have spent Friday Sat in a studio and moved to a 1 bedroom for the rest of the week. It saved us a lot of points, but it was in the same building so it wasn't too much work. Still you have to pack and up pack.
WDW is very good about moving you, so it isn't that hard. It can be done with out a car, but is easier if you have one.
It comes down to packing really, and not unpacking too much. Packing in stages works well. One bag for the 1st stay, one the 2nd resort etc.... The less you have to unpack, the less you have to repack to move. The whole packing in Ziploc bags works well in this situation. When the weather is unpredictable this can be harder.
Our may trip is going to be like that. May 4 and 5 at some resort (value maybe) May 6 to 10th on the ship, May 10th and 11th some WDW resort again and then fly home. This is a lot of moving, so ask me in June how it went.