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I lived in the Keys from 1990 to 2003 the best thing about it was the view in my rear view mirror as I left there, have not been back and dont want to.
You will be sorely disappointed with Key West.
Have been to both the other spots you mentioned, ok to vacation but would not want to live there. As to money Cancun will be the cheaper of the two esp if you get a rental and get away from the city some.
Todd
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