I've never lived aboard full time, but every time work sends me on a road trip, I look for the nearest body of water. Is it close enough to commute? If so, the boat goes on the trailer, and I spent a week or so camping aboard and commuting to work.
It was fun, but I did have some difficulty managing my wardrobe. In my line of work I need to "look professional," and comfortable sailing clothes just don't.
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"It ain't all buttons and charts, little albatross. You know what the first rule of sailing is? Love. You take a boat in to sea that you don't love, she'll shake you off just as sure as the turning of worlds. Love keeps her afloat when she oughtta founder... tells ya she's hurtin' 'fore she keens… makes her a home." Captain Malcom Reynolds, Paraphrased