Yeah...it is quite doable if you can afford the time and the lessons. Maintenance is probably not that easy to learn but if you buy a boat with a good survey and get any survey issues taken care of immediately, you should e in good shape for living aboard as you learn. If you take a loan for the boat it will need to be surveyed and USCG documented. If you pay cash...you can simply register it with the state through DMV. You should ask about personal property tax as some parts of tidewater have it...and others do not on boats. Locally the Hampton Yacht club may be a good place to inquire about instruction and a good source for sailing buddies. Nothing special required for liveaboard permits...just a cooperative marina manager! Welcome aboard!
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