I can go along with the cold winters, given that this is a retirement situation. I never much craved to make a living sloggin' thru the slush (isn't that a song?) having grown up in Michigan. I would also like some more hills in the landscape than Southern Florida has to offer. So where does that put us, somewhere in the Carolinas? Does that area meet the other requirements?
I am picturing subdividing a farm, leaving the farm house and/or barn to be the Community Center, with the rest of the land sold off in lots. I'm also picturing each lot owner putting up a duplex, one to occupy and one to rent out to another 'Catter tenant.