Liveaboard and Cruiser
Will, as you may know your particular plan is the hardest one to execute on a small, finite budget: buying a boat that offers both comfortable, relatively spacious liveaboard features AND is suitably designed & built for long periods of offshore sailing. There can be no compromises on each of the basic systems as well as the structure of the boat, and sometimes it''s surprising how much it can cost just to have a sound but basic boat (before the first piece of gedunk hardware goes aboard). Just to give a few examples, by the time you leave, the boat will probably require a new standing rig (and perhaps lots of new running rigging), the steering cables, bushings and perhaps chain will need replacing, you may have a structural issue to address (how old is that rudder? does it work on its post?), and it''s unlikely you will find the boat with an adequate, suitable suit of sails for such a trip. Since you will need to tackle these projects yourself ($$$), your time window isn''t as long as it might feel, given that you also have to find the boat and then sail her sufficiently thoroughly to come to know her before shoving off.
None of this is meant to disuade you from The Plan, but rather to suggest a context in which you take the next steps. Here are a few things I would do initially, were I in your shoes:
1. Buy Voyager''s Handbook by Beth Leonard and carefully review the chapters on boat selection as it relates to the cost of cruising, as well as the overall financial planning plan she offers. No one does this topic better than Beth and it is crucial to a successful fit-out, adequate cruising kitty AND financing the subsequent re-entry. While you have cruising experience, these issues may all be new territory for you.
2. Accept that ''smaller and simplier'' is going to be your primary theme and shape your shopping accordingly. By ''smaller'' I don''t mean "small" and I''d encourage you to think displacement before length, since that not only influences cost and ease of handling for a short-handed crew but also *may* define how ''big'' a boat truly is in the ways that are meaningful to you (volume, load carrying and such).
3. Consider a bias for boats that were prepped for cruising but where the cruising never ''took'' for at least one of the crew. Often these boats are initially selected thoughtfully, and so the design and build may be suitable. Second, the basics might have been already tackled. Third, they tend to congregate in returning yachtie locales and so targeted shopping can be efficient. Since you are apparently in the U.S., I''m thinking of places like S Florida, Annapolis, SF Bay and the Long Beach/San Diego megalopolis.
4. Use a broker (or several, if working different coasts) along with doing your own web work. Solicit broker recommendations from others and make your choices using length of tenure as a broker, preference for your kind of project (namely, older/cheaper/mid-size cruising boats; most brokers will want to sell bigger boats, or multihulls, or power, or...), and by chatting to them on the phone. E.g. I would recommend Al Gundry at Interyacht in Annapolis if you are shopping in the Mid-Atlantic/NE region; excellent knowledge of the marketplace and of sailboats, and 20+ years experience with Interyacht.
I know this doesn''t take you to a specific recommended list of brands & models, which is what you are asking for...but I think that''s starting at the wrong end of the logic train. Just as the previous poster illustrated, there may well be choices out there that are suitable to your needs but which you wouldn''t consider if starting out with the typical ''Island Packet/Tayana 37'' type list. Moreover, lesser well known boats might also have lower prices. However, I would recommend you review John Neal''s list of recommended design and build preferences for Pacific-type cruising, which does include a (now dated, biased to the larger vs. smaller) list of cruising boats. See http://www.mahina.com/cruise.html - very useful info IMO and of course John''s been cruising in the South Pacific for 3 decades now.
Good luck on the Big Search; it can actually be a lot of fun!