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!