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By all means do it. Especially if you're in the Chesapeake, although the winters will be a challenge. Folks liveaboard here in Toronto during the winter. It's not an easy life but most do it so that they can save enough to take off. My post was just a note on what happens in real life as far as sailing goes. If you liveaboard at a dock it generally becomes too much trouble to get things shipshape to go out for a sail.
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Rick I
Toronto
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