Such a great range of thoughtful and experienced replies. Thank you all.
Tackling Arne's question first - this boat will be a blue water cruiser I intend to take me anywhere an intrepid adventurer might want to go, from Scotland to New Zealand. It'll be my home for hopefully more than a few years. I think that there are perhaps some systems / goodies with which I could do without for a while, but as it's my home, I'll need it in pretty good shape before I splash.
I too, David, wonder if my skillset and large-project drive aren't more a curse than a blessing. I've built some decent sized projects, including a single-handed, simple machines only, 36 x 24 barn / workshop in which I was going to build a 28 foot cruiser based on the Graham Byrnes designed Princess Sharpie. (See, "alimony" above.) I tend to get itchy if I'm not working on something extensive. But full time cruising could be that extensive thing instead of mostly full time building. I think.
Peter's advice to only do those jobs that are fun, and set a time limit, is great. I was already planning on farming out the exterior fairing and painting - "soul destroying" is an apt description. I don't feel that much else is beyond my skillset except finish carpentry. I have no doubt that I'd make more scrap than art, and worse, my small mistakes will glare at me for years. (I tend not to see the slightly mismatched wood or gaps in other people's work, though. You know how it is.) Arne's point about focusing great quality on items with which we have a tactile and frequent relationship is right in line with my thinking; I don't skimp on doorknobs, light dimmer switches, or hand planes. But I don't need perfect finish in behind the locker doors.
I will say that when I was tearing up the interior, each part that came out was met with the thought, "Man, that's another 40 hours of careful fitting and finish work to put a comparable thing back in."
When my kids were young and I had to stay around the house, I loved large projects. But my kids are heading off into lives of their own soon, and I'd like to spend much more of my life energy on, um, grownup relationships, shall we say. (See, "alimony" above.) And that's hard to do if I'm, like Mark, working on the boat every night and eight or so hours during the weekend. What's bothering me is the opportunity cost; life is short.
Zane, I actually consulted with James Baldwin early on in the project - he's quite knowledgeable and has a great philosophy. I may contact him for this. Alternatively, I've already reached out to Tim Lackey in Maine, and we'll see what he says. But I've got to think that with Mystic, Connecticut and Newport, Rhode Island so close, there'd be a good collaborative shop nearby. Trouble is, the good ones are often a bit off the water and get trade through word of mouth. I'm going to the Wooden Boat Show in a few weeks at Mystic Seaport Museum. Perhaps I can get a few locals talking and make some recommendations.