billyjoe:
I saw a very good seemingly well-balanced article about second home ownership in the recent issue of Money Magazine this past weekend. I recommend that you look at that (I couldn't find it online but if I could I would put up the link). And then figure out how to get some good information about the SoWal market and talk to your accountant. Also, factor in taxes, insurance, etc., because they are expensive and the more expensive the house, the higher they will be.
We love our places (we bought two smaller cottages rather than one bigger one) and being able to come to our second home in SoWal when we want to (which is never often enough). When I'm working away or otherwise stressed in Michigan, I can think of the beach across the street and quickly calm down and get perspective.
We rent them out when we're not here, though you can't count on rentals as a significant source of income (even though the rentals certainly help, they aren't dependable given possible hurricanes, economic trends, overbuilding in the area for now, etc.). We bought (when the prices were lower) for the long-term, as places to enjoy and as reasonable investments over the long-term. So, short term economic cycles don't worry us. We're not in Grayton Beach, though, so others who are have a better sense of that beach (we're in the Seacrest Beach area).