Thanks, all; for the quick responses and the input!
My wife and i spent a blustery day checking out marinas and over a dozen boats, and quickly made some decisions.
First; a 25 is apparently not large enough inside for her ( looked at 3 Hunter 25's, none of which were those mentioned in my OP, an older Catalina 25, and an O'Day 23.
Secondly, Oyster Po' Boys are a great thing...even in the winter ( more on that maybe later).
We DID, however, find s boats that we both like and are in our price range. The first is an 82 Hunter 27 with the "deeper Keel" (4'3??). It has the Yanmar inboard, roller furling, sails in probably 70% condition, and seems to have no major cracks above the water line. The front hatch does leak. Overall she seems well taken care of, but certainly needs a bottom cleaning. She has shore power, a marine head, and comes with a hatch AC unit. Asking price is effectively $6,000.00; when I include the owner willing to let us reap the benefits of him having paid through 2013 for the slip.
The second is a Lancer 28, that my wife loves the lines of. She's had a rough life, doesn't have the roller furling, an older 2 stroke OB, and has been retrofitted with wheel steering that feels "clunky"...almost like the old rack& pinions felt when they slipped a gear. On the Lancer, there are some deep cracks at the aft cleat and winch on the port side, as well as cracks around the base of the mast. The Lancer has the Porta-potty, and overall looks. I could probably pick up the Lancer for around 2 grand; which would leave allot more money for the attention needed. She is in desperate need of a bottom job.
From all accounts ( including my Dad who lived on a H34), the Hunters are a slower sailing boat, but I'm not certain that a boat with a tendency to right itself and point windward easily is a bad thing for a new Sailor.
In either case, unless I can negotiate them down enough to cover some "worst case" repairs, I'd have the boat pulled to get the hull looked at.
Finally; thanks for the PM! As soon as I've been a member long enough....I guess the board will actually let me read it.