I am also someone that moves around from WDW resort to resort ALL the time and I have done it both with and most times without a car and it is SIMPLE. I agree the biggest hassle is not having a room for part of the day but even that you can work around if you plan ahead of time and I have found the earlier I check into the next resort the better. I usually get up and check into the new resort and then come back to the old resort and get the family up and moving. Many times we make the moving day a down day and will give our baggage to luggage services for transfer, while we keep a bag with pool things and we have a nice breakfast somewhere and then we go to the new resort and just hang by the pool and relax. Most times our new room is ready by mid afternoon which is about the time we are ready to leave the pool and take showers, unpack etc and then go out for the evening. I MUST add though, I did not start switching WDW resorts until about 9 yrs ago when my kids were 10 & 12 yrs old, so switching has always been easy because of their ages, when they were babies and toddlers we checked into the trailers/now cabins at FW and planted roots and never even thought of moving until it was time to leave for MCO. LOL! So I can see where for a family with young kids switching resorts could be a big hassle but for adult parties or parties with older kids, switching resorts could not be made any easier than Disney does it.