If anyone still cares, lol...here's the update on the "mint" 27 ft Catalina I saw yesterday.
Mint maybe a strong word but It's exceptional. The owner was a boat freak, he had every do-dad from winch covers, to two bilge pumps and just about anything you could order from Catalina direct. Window shades for the inside, I could go on for ever about the $$$ in accessories you hardly see on boats and some stuff he had two of, one stored and one in use.
New diesel engine in 2005, 4 new deep cell batteries, complete bottom job in 2008, all new sails in 2010, new bimini tops in 2011 (there are two so the whole cockpit can be covered), all new lines/sheets, in 2012, everything cushion reupholstered in early 2013 for a grand total of $22k in slips presented in a nicely package in a book. Oh, did I say a custom made traveler above the hatch way and all new self-tailing winches....
The boat is $10,000 firm-
We took the boat out and sailed for three hours and my thoughts, the boat may be to big for me being a newbie and probably single handed sailing 85% of the time.
I need to give this serious thought and this experience may push me back to a Catalina 25, which feels way smaller and more manageable at least for now. I'm scared I could regret it and pine for the extra room and size if I ever find a lady friend, lol...
Let me make a bold suggestion here.
People always make extraordinary claims about how many great boats are out there to be had for peanuts - $3000, $2000, free. FWIW, I think most of it is hogwash. Boats under $10000 almost always need a lot of work to get them into the kind of shape that someone can be really proud of (and confident in, since your life may depend on that boat). This is true of all brands, including Catalina. (It can be argued that this is especially true of Catalina, since there are so many that have been out there a very long time.)
If you've found a boat for $10,000 that's truly in great shape (as you've described with this boat), go get it and don't look back. You could spend a year finding a boat for a few thousand less, and end up having to pay another $5000 for unpleasant surprises.
Be realistic. This guy loves his boat. He's used his boat recently (as opposed to most boats that have sat neglected for several years before the owners got around to selling.) The fact that he was able to take you out in it right away means it is in sail away condition. Sail-away condition means you'll spend your first season sailing, instead of working on a boat endlessly before you have any joy.
Unless you REALLY think you want a significantly different boat (much smaller or much larger), you should go for it.
I can virtually guarantee you won't find a C30 in sail-away condition for $10,000 or less. When I was looking 4 years ago, I found some C30s on Craigslist for $15,000-$20,000, and they were all moldy wrecks. (Of course, their owners claimed they were in turnkey condition.)