Re: Starting From Scratch...
What you'll learn if you hang around here for a while is that what's good for long distance sailing isn't (generally) good for long term living aboard. There are design considerations, like long keels, narrow beams, small cockpits, etc., that make "blue water" boats excellent for crossing oceans, but not the best when it comes to actually being a "home". What you might want to consider is a "coastal cruiser" like the aforementioned C30, or even the "Cherubini-era" Hunters that Captainmeme suggested. High points for such boats include the fact that their draft isn't TOO deep, which will make them good choices for the shallower waters that you'll find in that area, and there are a TON of them out there, with lots of third-party support when things go wrong.
I suggest that you look at the nautical charts in the areas you're considering and figure out what the typical water depths are at low tide. Then look at SailboatListings.com, Yachtworld.com, and SailboatData.com to get a sense of what boats are available in your area, what their prices are like, their general condition at any given price point, and what their draft tends to be. What you'll probably find are quite a few C30's and H30's, and a few slightly larger too (largely for the reasons set forth above). Start there, read up about them, and then find a few that are for sale and actually go aboard them (find ones that are already at the broker's marina if you can, this way you aren't wasting too much of the broker's time). Sit in the cabin and ask yourself where your "stuff" will go. How many shirts, shorts, dresses, undershirts, suits, etc. can you pack in the dressers/closets? What about foul weather gear? Supplies? What kind of shower is there? Does it have room for the appliances (TV, blender, etc.) that you want/need in your life? Can you see yourself cooking in the galley?
Those are some of the day-to-day things to think about. Then there are the bigger questions, like visitors. Will you have day guests, or overnighters (kids/grandkids)?
If overnighters, where will they sleep? How much of a PITA will it be in the morning if you have to break down their bed before you can eat breakfast, or before you can get to the head? Are there enough heads so that you and your SO can go to the bathroom at the same time? (don't think that's an issue? Wait 'til you both eat some bad seafood)
If the guests are more likely to just be day visitors, how is the cabin set up for lunch/dinner? Is the cockpit big enough to comfortably hold the number of guests you're envisioning?
Of course, the answer to a lot of the issues above is to go bigger. But that will compete with your desire for a singlehandable boat. What you'll find is that as the boats get bigger the sails and other "stuff" gets heavier/harder to lift. You wind up with power-assisted winches, windlasses, etc., and that adds complexity, increases maintenance needs, and adds to the cost.
Then there are the costs associated with actually keeping and maintaining the boat. Slip fees are expensive, moorings less so. But then how do you get back and forth for provisions? Are you OK with taking a dinghy back to shore in a nasty rainstorm because you forgot to buy toilet paper the last time you were at the store?
In the end, these kinds of competing priorities are what keep many here with boats in the 27-35' range. Anything smaller is too small to really live aboard comfortably for any significant length of time (at least for me, YMMV, and that's fine). Anything bigger, and the costs can really add up quick.
To be clear, I'm not saying don't do it. I'm saying take your time and really start defining how you think you'll use the boat, and what living aboard will actually mean. Once you do that, you'll start to find the boats that will actually be appealing and useful to you.
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1980 Allmand 31
1975 Albacore 15
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