Join Date: Nov 2007
Location: SF Bay area
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Re: Want to retire...young.
Yes, you can do all the things you suggest, but everybody who warned you against buying a "project" boat are absolutely right... unless you are already skilled in all the things that a project boat requires. There are people who worked in related fields and were able to buy a boat that needed a little work and do it themselves. But if you haven't worked with wood or fiberglass or don't know much about motors, getting a project boat is a mistake. You'll be delaying your dream by years, because you won't be able to learn about sailing in this period.
Your best bet is to get some experience on OPBs. A sailing co-op is the best option since it's very inexpensive and you will be responsible for maintenance, which they will generally teach you. There will be occasional group sailing activities and you get get some sailing experience there, or you can just go take a couple days of lessons.
Your next best bet is to buy a small, inexpensive boat that needs no major maintenance but is otherwise getting old and tired. Ideally a boat that can be pushed by an outboard, which is much more easily replaced than an inboard. Pick something that is minimally fitted out (rig in good condition). In your area you can definitely hire somebody to give you lessons on it. If you want and you can find a marina that will allow it, living on board will save you some money, which can be poured into the boat or saved for your life at sea. Of course, there's no reason not to delay this a couple of years as you build up savings and experience with the first option.
Finally, remember that you have to eat, bathe, etc. while you're living the dream. Where's the money for that going to come from? Is your job the kind you can leave for six months and then pick up again? Can you easily get hired to do a similar job in a different location? If so, you're probably good to go. If not, then when your savings run out you will quickly start regretting the decision.
I'm in a very similar place as you, just a little further down the road. Four years ago I took some lessons and got a cheap boat (in that order). Figuring out where the money's going to come from, not just tomorrow but also next year and the year after, is really the only thing that keeps me from casting off.
s/v Laelia - 1978 Pearson 365 ketch
s/v Essorant - 1972 Catalina 27