I'm moving 4 times when I go in a week or so. I hand my bags off to Bell Services first thing in the morning, and then head off for the day. I return to my new resort around midday, and get checked in.
With a car it's a no brainer...just pack up the car and drive to the next resort. That's actually the very best way to do it...little time is wasted and if you have the right car, you can leave everything in the trunk until you get into your room, which saves you tipping for baggage delivery.
Moving is easy if you don't bring a bunch of stuff and only move once during your stay it is fine. DW and I did three moves in one stay and I would have to vote against more than one move in a stay.
If you can't get the rooms and need to move around in order to go I would but if it can be avoided I would limit it to once.