From watching various youtube channels made by people sailing around the world, such as the excellent S/V Delos channel, I've learned that if you want to be a sailor you have to really enjoy boat maintenance. If you're one of those people who would fix crap on a boat and do small engine maintenance for fun in your spare time and even go down to the local machine shop and learn how to custom make parts just cause you liked it -- if hauling your boat out of the water to sand it and paint it while wearing protective gear makes you feel proud -- then sailing is definitely for you.
Well, maybe, though round-the-world sailors and daysailors are kinda apples & oranges. The hours-spent-having-a-blast to hours-of-maintenance ratio on something like a Hobie 16 beach catamaran is ridiculously high
Yep, it really depends. If you get something old and made of wood, you're probably signing up for a lot of maintenance or a heap. There are plenty of heaps at marinas if you go look. The alternative is to get a boat guy, which is also expensive. The other other alternative is to join a sailing club which collectively maintains the vessels. There are plenty in the Bay Area if you look :)
So what you're saying is, based on what he actually spends his time doing, "sailor" is basically a euphemism for "boat repairman"
More like being a boat mechanic is an integral part of the experience of owning a boat. Some people like working on cars, while most people take theirs to a mechanic. If you're the former kind of person then you're probably much more likely to have a satisfying boat ownership experience, especially if you buy a used/older boat.
Similar sentiment, but the old saying goes something like:
"The two best days of boat ownership are the day you buy it and the day you sell it."
You would need to bring out three thousands, per month, before you break even with rent in SF :).