I'll guess that I will ad my $.25 opinion which is why I assumed that you posted in the first place. Within your stated budget I would focus on a boat in the 35 to 40 foot range that represents a reasonable level of quality. Much above that length and it becomes more difficult to manage by one person and costly to maintain and operate. I have also done a fair amount of research, unfortunately I can only be content to dream at this point as I am lacking the financial resources to make my dream a reality. You might want to look at boats with more modern under bodies and fin keels. Yes, heavy full keeled boats are stable and track well but are miserable to maneuver in a crowded anchorage or dock
in cross currents. Besides as Robert Perry has been oft quoted as saying "There is nothing wrong with being able to go fast". A few older fin keel
boats that I would suggest that you look at and that will allow you to stay within budget even after outfitting properly are a Wauqueiz 38 also known as a Hood
38, a Wauquiez 35 (mid eighties version), CS (Canadian Sailcraft) 36 to 40, Sweden
36, Valiant 37 and 40, Cooper 416
and the Kelly Petterson 44. None of them are perfect but they are all of reasonably good quality and have been out in the big blue. Full keel
boats that fit the bill are the venerable Tayana 37
and Baba 36 but they have too much teak
to maintain for my taste and look for those that have had their teak
decks removed and or have been repowered with adequate sized engines as many have been repowered with under sized plants.
But has been pointed out by others you need to focus on your priorities and spend a lot of time on Yachtworld, Latitude 38, reading reviews
on sailing forums
and consulting the numerous books
written on the subject. Speak to boat owners at your local marinas
in SF. Most are happy to talk your ears off about their boat. I found most boat brokers with the exception of a few were not helpful as they were more interested in selling you a boat, any boat, than in finding you a good fit. Good luck. It sounds as if you are headed for a real adventure.