Late Start Revised Plan
 

It's clear with my 11 year old son I can't move to the villages for 8 years; but with market depressed (I have no idea about if it's the same in the villages but I will assume home prices are down) would it make sense to buy now and rent until I'm ready? I don't care if it doesn't cover as long as the shortfall isn't ridiculous.

There are several here that rent now so that they can live here in the future. Seems to work for them. Some have paid cash for their house, most of them have mortgages and the winter rentals at least cover the mortgage for the year. You can also look for long-term renters.

I don't think TV has taken much of a hit in the housing market -- at least not like the rest of the country. It may take a bit longer to sell a pre-owned house, but sell it does if priced properly. New homes still seem to be selling briskly.