We did it this last trip. The actual check-out/check-in process is pretty painless and Disney moves your luggage for you, but I would NEVER, EVER do it again.
I still had to unpack when we got to the first hotel and take the time to pack up when it was time to move to the next. Then I had to unpack again and repack when it was time to go home. We're a family of 5 and that's a lot of packing and unpacking. I found it to be a PIA!
DH and I decided that it is better to just settle and use the next resort for the next time around. He didn't even do the packing, but just when you get used to everything, it's time to move and start over. It also made our Disney trip just seem so much shorter. Kiddos didn't like it any either.
And our trips our 10 days, it's not like we spending one or two nights in each hotel. Just not worth it *for us*.