Lots and lots of good advice here. I'll add one more thing. When I was growing up we had a condo in Miami and went down (from Chicago) several times a year as we had lots of family there. We rented it out only occasionally, but once a renter totally trashed the place. The security deposit didn't even begin to cover the damages. And this was a respectable businessman who was not that young, screened by an agent. You just never know.
I can't stress enough the difference between having young children (7 or younger) and having older children. Once they are older the travel possibilities are endless. We have taken our DD so many places and she has learned and experienced so much. I just can't imagine limiting our vacations to the beach or nearby mountains. And as another poster said, VRBO can be your best friend!
Good luck.
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