You're rushing it, but if you must...
Levin, you are apparently going to a post-commissioning school (which one?) and will only be in SD for a year. Some of that year will be used while finding, purchasing and settling into your boat, some of it will be taken up by trying to sell it (you'll probably want to move off during that period so the boat can be shown, will look presentable, etc.). That leaves a pretty narrow window to use it and experience the lifestyle you are imagining.As a young family of 3, we at one point lived on a 20 footer; we even enjoyed ourselves (most of the time) and I'm now living aboard for the 4th time, so I don't think I'm biased against the choice. But living on any smaller boat (<35') with a 9-5 regimen, even in mild SD, is the least pleasing residential option of those available. Boats, and especially small boats, make bad apartments. If you chose a smaller boat like the Catalina 27, you'll find it takes much effort, time and organization just to have room for the things you'll need. It will then take more time, cleverness and effort to make it possible to sail the boat without everything ending up on the cabin sole.You lack boat skills & systems knowledge and so can forget about someone choosing you to stay aboard & look after their expensive boat. And chartering is going to look to your checkbook a lot like renting an apartment, except perhaps cheaper. SD rentals are expensive, even after your BAH offset is considered.Moreover, as you've heard elsewhere in this thread, a 'real' liveaboard slip is going to be hard to come by unless you choose to restrict yourself to purchasing ONLY the boats currently being brokered, solely when you show up in town, that convey slip rights AND a liveaboard option. You may get lucky but, within narrow budget parameters, the inventory of choices will probably be very slim, indeed.The best part of this thread (if I place myself in your position) are the personal referrals being offered. Networking is by far the most viable method to use in any setting when resources are scarce, you are scrambling to climb the learning curve, and your in foreign territory. I would work each of those referrals hard, to see where they lead.Here's what seems to me, given your 'druthers and limited time frame, a far better option:- show up and book into the Q for the max time they'll allow; as of 3 years ago, this was very short...but work it for what you can- network with the command to which you're reporting and look for JO 'ranch'. This is a common JO set-up in SD, usually a rental home that multiple JO's share and where turnover is routine and short stays not tough to work out as tenants deploy, do a school elsewhere, TAD, etc.). Move (if the Q can not accommodate you) into a ranch that's convenient to a) your school and b) the main yachtie area (Shelter/Harbor islands)- Your school commencement date will be fixed so you need to arrive in SD soonest and front-load your efforts to meet those you have already corresponded with, suss out the marina locations, begin looking at boats, etc. Expect to make a series of uninformed or quasi-informed decisions if you take any irreversible steps now (unavoidable, given your haste and ignorance...but hey, you're young and can probably recover from anything). Try to do enough front-end work that, by school start date and before that experience envelopes you, you can revisit your initial plans and test/confirm/alter/scrub them -As part of your front-loaded research, visit the Navy's sail training facilities and get a good feel for what Plan B might look like if you sustain the longer term plan to liveaboard but only want to learn about boating in the short term. Doing this will give you a feel for Plan B.-If Plan A still feels right, consider buying a small boat, something like that Catalina 27 (ubiquitous, easy(ier) to sell. A special deal like mentioned in this thread may be just the thing, even if it will be dirty, poorly maintained and in need of much TLC. And then, while living at the ranch, try periodic liveaboard spells on the boat. Each marina will have its own rules (none of which will probably be rigidly enforced; 'Sneakaboards' are a common California lifestyle) that permit limited living aboard, a good way to avoid the 'must have a liveaboard slip' dilemma. Test the lifestyle and see what you think, all the while becoming more familiar with the berthing options in town and what might be possible if you choose to move full-time to liveaboard status. Plan to fall back on another Ranch option when getting the boat ready to sell...or trailer it to the next duty station, I suppose.You may not have the $$ for this approach, but it's one that will get you most of what you THINK you want given the circumstances you'll be facing, and allows for wiggle room in the timing of things. IMO if you buy, the hardest part of the plan will be to get out from under the boat, especially if you transfer and then must deal with the boat from a distance (slip rent or storage fee, distant broker not highly motivated by the small commission likely, insurance premium et al.).Don't forget that all this advice you are getting is not free. You owe the group some periodic follow-up reports, so we can all learn what you do as you go forward.Good luck to you!Jack