36 Cascade 1988
I have a Cascade29 that I use for island cruising in SoCal and that I also (pathetically) race. Most of these boats were owner finished, so fitting out quality can vary wildly. The maker is reputed to make bomb-proof hulls though, using nothing but hand-laid directional cloth. There''s lots of anectodal stories of these washing onto the beach in Cabo and being towed off unscathed, or T-boned by a MacGregor65 and nary a scratch, or an at-sea collision with a freighter with just a bent bow roller, or a propane explosion that blew out everything but left the boat essentially structurally sound, or a salesman bouncing .45cal. slugs off the hull, etc. So although they were owner finished, the company (still in business) seems to have provided the support the owners needed to get the job done adequately. There have been a few folks that have sailed the 36''s and even at least two of the 29''s around the world.
Jim Moore''s book "By Way of the Wind" depicts how he and his wife built a 36 and then circumnavigated it in the early ''80''s. He basically tought himself to sail by book while building the boat, and then through experience once they left. Not the usually recommended method, but he made it work.
Ed Hart''s story of his solo trip around in a 29: http://solantamity.com/Extraneous/MuggingsPlus.htm
He''s a gung-ho ex-Marine with more guts than sense- he left for Hawaii with a broken boom, figuring it would be easier to repair it in Hawaii than panama. it took something like 45 days to get there...
That''s just general stuff about the boat type. For any boat purchase, get a survey, absolutely! You''ll learn lot''s more than you''d ever find yourself, and have all the boat''s problems presented to you in a checklist fashion for reference as you prepare the boat for the trips you are planning. And a surveyor will spot problems that might be deal-breakers, or useful for negotiating the price.
As for sailing experience, these aren''t generally hi-tech boats, and can be sailed with broad levels of participation. Some folks might just roll out the genoa and reach around the sound for an afternoon, others will want to learn how to raise and optimally set all the appropriate sails on every point of sail. This boat probably is geared more toward the first guy, rather than the second. But it will tolerate you experimenting with the other sail adjustments, and probably not break on you. It just won''t reward perfect trim with spritely acceleration.