Good for you! I have a few thoughts for you on this....we''re planning to head south ourselves and spent a good deal of time researching affordable boats, budgets, etc. I''m 35 but in my 20s I sailed transatlantic, down W side of S.America from Jamaica, to the Galapagos from Panama. (Just to let you know that my advice isn''t ALL just theory!)
For one thing, read a bunch of books. For fun, and ''cause the guys are roughly your age, I''d recommend "Dove" and "Lionheart". Also Tania Aebi''s "Maiden Voyage" might be interesting. Read "Desirable and Undesirable Characteristics of Offshore Yachts", & "Heavy Weather Sailing", for sure. (You can get these books cheaply on ABEbooks.com or bookfinder.com, used books, or ask you library to get them for you if they don''t have them...) Another resource I HIGHLY recommend that will be immensely valuable in looking for the right boat, evaluating it, and fitting it out, is Nigel Calder''s "The Cruising Handbook" it is GREAT. Spend the $$ on that one for sure.
OK, boat prices. If you have only $30,000 to spend on the whole boat, including making her seaworthy, I would not start out looking at 39 foot boats. For one thing, no matter how well-cared for the boat might seem, it is going to need some money put into it before you make the trip. A decent liferaft costs over $3k, for instance. You might need new batteries, or a new GPS, or a SSB/Ham radio, or a new sail...etc etc etc. A 39 foot boat will likely have much more complicated (and bigger) systems, which are much more expensive to maintain or replace. We are sailing with our daughter, and were bummed sometimes because there were a lot of great boats that would have suited us for substantially less $$ if there were only 2 of us.
With 2 guys you will probably be perfectly happy if one of you takes the V-berth and the other takes the quarter berth or pilot berth. Also, think about the level of luxury you really need. When I was your age I was a lot more willing to "rough it" in some respects than I am now!
My point is, if you look at smaller boats, you will be able to afford a VASTLY better built and more seaworthy boat for $30,000 than if you set your sights on something as big as 39 feet.
As far as design characteristics, again I recommend reading "Desirable & Undesirable...(above)" and Calder''s Cruising Handbook. Some people feel fine in a flat-bottomed, deep-keeled, spade rudder speed machine; others won''t go to see in less than a full keel, wicked heavy cruiser....personally i feel much more comfortable with a decent compromise: a long fin keel or full w/cutaway foot, skeg-hung rudder. I''d steer clear of ferro-cement as a hull material: fiberglass or aluminum are best for cruisers and fiberglass wins for easy maintenance. External lead keel would be preferable. Go for a cutter rig if you can find it, for versatility of sail plan and heavy weather sail setting. Ketch might be good, but wont go to weather as well. Above all, get a WELL built boat. if you are going to sea you don''t want a boat that was built for coastal cruising. And while there are some fabulous deals on very sound and lovely cruiser/racers from the 70''s, be careful about boats that pushed the IOR rules to the limit and are not safe (the above books will explain that...)
There was a recent thread on this ($30k cruising boat) on the Cruising World bulletin Board recently... you might want to look it up in the archives.
Here''s a partial list....
If you can find a Hallberg Rassey in your price range, check it out. Swedish built world cruisers.
Other well-built bluewater boats include
Albin Vega (though may be a bit small for you)
Contessa (though may be a bit pricey)
Some solid UK-built boats:
Westerly (the 32'' Renown has 2 cabins, kinda akward looking but great privacy!) also 31'' Berwick
Sparkman & Stephen''s designs that might do, pretty well-made though not top-of-the-line:
Tartan 34 (keel/centerboard)
Chris Craft''s 37'' Apache, or the 35'' or 32''
Other fairly decent boats:
Bristol (maybe Bristol 30?)
Cheoy Lee, various designers and built in Taiwan, I think....pretty, several have crossed oceans, but notorious for leaks, esp at deck.
Challenger...don''t know much about them. West Coast boats that seem appropriate. Not top-notch bluewater but maybe OK for your trip.
Allied Princess 36'' or Seawind 30''. Kinda pokey but several have circumnavigated.
and last but not least: various Pearson models such as the 323 or vanguard. Actually, the Vanguard might be the PERFECT boat for you. late 60''s, early 70''s, very solidly built, sails well, etc. Dan Spurr ("Upgrading the Cruising Sailboat" and other books and magazine articles) I believe had one, and there''s the famous Mollymawk often featured in Cruising World magazine.....sheck it out!
Remember that any older boat is going to have issues you''ll need to address. most of these boats have cored fiberglass decks and all the previous owners did not keep up with thier deck-hardware-rebedding, so there are bound to be some rotten core areas you will need to repair. 30 year old standing rigging should probably be replaced, and chainplates removed and checked. Et cetera.
Have fun looking and good luck!!!