Buoyant1
Contributor
The upper Keys are definitly an option. You can pick up real estate down there for a SONG right now as people can't afford their second home anymore and a significant number of homes down there are indeed second homes. I had a beautiful large, older, single family home on a HUGE lot in a heavily wooded subdivision and you may be surprised at what you can find. It's less than half an hour to the mainland with all of the shopping that you can't do locally and not far from MIA. However, my advice to rent for a year still sticks, if you chose the Keys you might find it too remote or with not enough nightlife. Again, it depends on lifestyle.
If you want to live in a beautiful gated townhouse/condo community in Key Largo, with its own marina, boat ramp, and fishing pier, and even a sandy beach, pm speargirl here on the boards and ask her about Kawama. She is a realtor who does rentals in there.
My wife picks up real estate books whereever we go down to the Keys and she noticed that most of the houses in the Upper Keys are about 25-30% cheaper than they were last year at this time. In fact the place we stayed in Marathon last year (well and this year) sold for about $750,000. There is a comparable unit for sale at around $450,000.