We casually began talking about it maybe 2 1/2 years out. Serious planning about 12 months out. We purchased extra
DVC about 2 years out, and other timeshares about 1 year.
Our original thoughts were to stay at DVC for 6 months and then go back to work in Florida and the idea just grew and grew. I figured out we didn't need to work if we would be happy with my retirement and savings. We NEVER missed the extra money.
It is surprising what you can give up not to have to work.
I don't miss having a new car every year
I don't miss owning a private plane (maybe just a little)
I don't miss paying a large income tax bill
I don't miss paying state and city income tax
I don't miss the big house
I don't miss wearing "work" clothes and $50 "work" lunches
I don't miss flying to Florida every three day weekend - I live here now
I really don't miss much about my "work" life!