OP one thing you haven’t said, how many SF would you feel comfortable to live in? At $300,000 think 1140sf. High season rental start at $4,000 and up Jan-Apr. …
summer is much less, but do you really want to be in FL in 90 degree plus days.
If your plan is less than a month per year, for 10 years. Put away $1400 a month ( the funds needed to run a base home in your price range) in an account that you can make money on.
In 5 years TV could be 10 miles south of Eastport by then. Homes south of 44 will be 6 plus years old. Young enough not to have to gut and start replacing major things, old enough that lots of improvements made, that the owners will never recoup. Then make decisions, of course consulting with your financial guy would help you make smarter decisions.
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