Greg, I don't mean to criticize sailing schools and I'm sure some formal instruction would be useful to you. But most of the challenges you face are w-a-y outside a typical
school curriculum. Insofar as structured education is concerned, I'd recommend you instead book a leg with John Neal (visit
www.mahina.com) on a real cruising boat in a true cruising venue consistent with your plans. Yes, it will be expensive...but it will erase a lot of misconceptions (in fact, it might save you the cost of a boat you end up not needing!), orient you to what's necessary vs. nice-to-have, and teach you a lot about "cruising" (which encompasses a much broader range of skills than "sailing").
Buying a boat that's previously been cruised sounds like conceputally good
advice but the devil's in the details. Most cruising boats these days are loaded down with stuff you can't afford, given your
budget. Most 'stuff' has been owner installed, but you don't yet know what to look for. Most cruising boats these days are bigger than you need or can afford. And so forth...
The best
single thing you can do is get on the
water, as has been suggested multiple times already. Use Latitude 38 religiously, attend their crew-finder parties, read the
racing skeds so you can seek
crewing positions, prowl the
boatyards to offer weekend (free) help in exchange for
crewing opportunities, visit yacht clubs and ask about signing up for
beer can races...the list is endless and L38 always is offering suggestions on how to get on the water. If you can't find the time or motivation to do this a LOT, then perhaps you like the idea of cruising by sailboat more than its reality.
I'd encourage you to seek a berth on the
Baja Ha-Ha that L38 sponsors each fall. Even if you can't book
passage on a boat leaving
San Diego - which would be idea because, given your location and timetable for leaving,
Mexico is about as far as you're going to get - being able to crew a boat South from the Bay Area would be good experience and introduce you to what another owner's done in prep for cruising longer-term.
Begin assembling a good basic reference library that will help educate you on picking, equipping and sailing a cruising boat. Beth Leonard's Voyager's Handbook is a good one because she tackles topics life
financing your
cruise and does a nice job of offering cruising 'models' that are based on smaller boats with few systems and smaller budgets. Nigel Calder's Cruising Handbook is useful as an educational tool; just don't get trapped into thinking all those gizmos, systems and toys are going to be useful for you. For a very few bucks, I'd buy an old copy of Hal Roth's After 50,000 Miles - its full of sound
advice and was written at a time when boats were simplier and the emphasis was on seamanship and not on electrons, bow thrusters and satcom systems. There are many other
references; dig into them and see what you can learn.
Good luck on the
research...but get 'out and about' and dig into some good
references to help with your basic education. I'm afraid that BB advice like mine is only skin deep.
Jack