At ~$100k, a 40-foot sailboat seems like a reasonably affordable option for housing in SF.
There is nothing about a boat that saves money, ever. It's an incredibly rewarding hobby if you're into it, but not cheap!
If he had done the same thing in a saner real-estate market then maybe by now his sailboat habit would have cost him as much as a flat would have, only later. But in the SF Bay I'm pretty sure he never would have caught up, and this way he's the lord & master & captain of his own tiny domain.
I know some people who do, and they enjoy it. Some of them even sail their homes, or take off to Hawaii for a few weeks in their home.
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5). An odd shaped hole in the water you throw money into.Source: I owned a 25 foot sailboat.
"The two best days of boat ownership are the day you buy it and the day you sell it."