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Originally Posted by nightfighter
First off, I would recommend downsizing to the New England home you would return to for summers. Then you spend winter vacations in various spots until you decide which one is right for you. That process might take you into retirement years, when you could be renting for a winter.... Better to make a mistake renting as opposed to buying IMO. Having absolutely zero experience with vacations down south over the past twenty years, I will say I saw some attractive areas surrounding Savannah when I've been down to see my daughter at Savannah College of Art Design. I have also been in some steamy heat there in June.....
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The older I get the more heat I can tolerate, but 4 months of 93 and humidity isn't for me. I definitely won't be rushing into anything and do plan a few winters of renting south to do some exploring, we may just decide that renting in a different spot for 4 months each winter or a couple years back to back is a nice way to explore a different area. In a way, I like that idea and the flexibility that comes with it, be nice to see new water, new golf courses, new local places and faces every other year.