Depends if you have a package (
DDP particularly) or small children! Bell Services will move your luggage, so that part is easy. However, you probably wont have access to your luggage until 5pm-ish.
If you are on DDP, you need a ticket package at each resort, making the cost of tix more expensive. Also, you will need to take time to check in first thing if you need your dining credits on moving day. If you have AP or military tix, this won't be an issue, unless during free dining.
On moving day, you will be "homeless" until your room is ready, which could be late afternoon. Annoying if you need a nap/break.
If small children are in the mix, split stays are a PITA IMHO, as more gear, packing and logistical planning are required. The older the members of the party, the better. It is also a PITA if you like to settle down in your resort... you may never feel settled until you move, and by then your vacation is half over.
It is a fun way to stay at multiple resorts, especially if your vacation is longer.
Just depends on your vacationing style and expectations. Happy planning!