Re: Renting vs Buying
Rented a designer for month of July, 06 (mostly to see how the Florida summer felt)...and, ended up buying a house on July 7th. No regrets...thoroughly enjoying the people, activities, and climate. We also had a 4,000 sq ft house but only used half of it, so, "downsizing" to 2,000 sq ft was a piece of cake.
Living here for real is as much fun as the preview program.
But, family concerns and some of the other issues you raised might make you a good candidate to rent first...if you have the means, then rent while still owning your house is probably the least risky. Unless, of course, your intent is to sell your big house no matter what. In today's real estate market, you should sell first (which is a challenge in itself) before you buy down here (or anywhere else).
It is a huge decision and I would say that 90+% of the people who make it are happy with their choice; the others had regrets and some move 'back home' or elsewhere.
Good luck to you.
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Maryland (DC Suburbs) - first 51 years 
The Villages - next 51 years
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