JD,
Recently lived in Key West for about two years. On the surface it's paradise, with a lot of positives, but financially it's unforgiving.
Your average Joe requires at least one job to survive there, and a roommate/housemate to split rent. If you're wealthy enough to afford a nice house, all the town's temptations will drain your checking account. That's the catch: so much to do, but so damn expensive to do it. (Everything from gas to food costs more there.)
I loved Key West, but might as well have tossed my wallet into the Gulf.
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