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Re: Getting the right size...
I went from living on a small-ish wooden 27 footer to an "enormous" 32 footer 19 years ago, and still haven't filled it up. As some have said before, beam, and the length that it is carried, is significant, and I'll add that the storage space is critical. My Westsail has relatively little living area, since the lockers are so deep, but I'm glad all that stuff is secure and out of sight.
When it comes to size for cruising, as compared to living aboard, I think there are additional considerations, not the least of which is will she carry a dinghy on deck or davits? And for living in a marina, it's not the size of the boat - it's the size of the dock box that matters!