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Darius,
Deciding on a boat is an involved process. I sent years looking at different boats, in person, in adds, and in compilations of reviews such a Pratical Sailor's volumns. All the while chartering on a variety of boats over a 25+ year period. The boats that I lusted after changed and in general grew in size. Doing it somewhat "cold" with out actually having a lot of experience has got to be tough. In the end I more or less bought my boat on the spur of a moment when I got the oportunity to get a hard to come by mooring up in Boothbay Harbor ME.
One thing that changed over the years was the need for more comfort and space. I would think that this would be especially true for a live a board.
I have chartered several Cape Dory 36's and they are a great boat. I think with the cutter rig it would be suitable for single handling. The Cape Dory owners association has a very active site and there is an active livaboard member with a 36 so you might get some specific advice there capedory.org.
Before you pull the trigger I'd suggest you think about some pilot house models. You'd be surprised at the variety that is out there. One thing I often disliked was needing to stay below in an anchorage with out any view of the out side in bad weather. Pilot houses greatly expand your living space and many do not have that "cluncky" or tacked on look. There are a lot that have a very salty look. Three is nothing that beats sitting in my pilot house on a cold rainy morning drinking my morning coffee dry and warm.
Three very different designs that can give you a ideal of the variety are Corbin 39 PH, Mariner 35 PH and a Fischer 36. All very different. Good luck.
Joe
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