Well, of course my favorite is Naples - as I haven't found anything NOT to like. Such a beautiful city - probably because it was founded by the rich and everything else is pretty new. Sooo much going on all the time. Arts and Craft shows every month - entertainment in the park, something going on downtown twice a month with entertainment.... just on and on.
Of course that price range would only get you a 2 bedroom in the burbs. However, I have a 2 bedroom condo (where the working people live) accross from a shopping center that I will be selling for $75,000. I have rented it for quite a while, and it will be available as soon as it I completely redo it.
Northen Florida is quite a bit less expensive....... but it is too cold for me in the winter.
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