I love real estate, but I like my investment properties close. I'd lean towards buying something close to home and renting in FL. It will be cumbersome to have a property that far from home especially on a short term rental basis. You also need to consider that most home owner's associations frown on transient rentals. I see many that require a min. of a six month lease. I don't think it will pencil out very well once you look at all the actual costs.
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Todd
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