There is a Disser that spent a year doing Disney and other timeshares for his retirement. I think they sold their home and actually lived this lifestyle for that length of time. I believe they could only stay 30 days at each location. He has a trip report, logging how he did it. That was at least 4-5 years ago and I know it took him a lot of planning. I am sure someone will pipe in with a link to the thread.
DH and I have done 10 nights maybe 14...awesome!