Re: Please tell me this is a nutty idea so I will stop looking at this boat.
I was looking for boats in your area up until about 2 months ago. There was a very nice Pearson 27 for sale at Ferry Point Marina near Pasadena, MD. Well maintained, and everything looked great. The seller wanted $7000. I don't know if it's still available, but she's worth a look. The seller was a really nice guy, in the military, and headed overseas. The boat had been his uncles, but he realized that with his deployments, he just couldn't justify the expense.
I had a fairly specific list of things I wanted in my boat this time around (e.g. cockpit seating for 6), and the Pearson just didn't quite make it for me, but she was tempting. If you are interested, you can PM me and I'll dig up his contact info. I have no relationship with the seller, but just liked him and understood the situation he was in.
Other than the Pearson, I would generally agree with Jim McGee's advice; Catalina's a great boats for a beginner. We had a 1984 C25, bought it for $1000 including the outboard. We probably sunk another $3-4K into it (bought a new outboard), but that would still put you well under your budget. As Jim said, the beauty of Catalinas is that they have a very broad network of aftermarket goods. You can find a TON of equipment for them, and replacement parts are plentiful. Had I been able to find one in my price range, I would have been VERY tempted to go with a C30 this time, in part because of the positive experience I had with the C25.
Another to consider is the Islander 28, if you can find one. I don't think I've ever heard anyone say anything negative about those boats, except due to neglect by previous owners. As to that Tartan 27 you linked to, she looks nice in the pictures. And a 15 year old boat may be more of a handful than a well cared-for, or recently renovated, 30-40 year old boat, depending on what the owner of the younger boat did to it (or didn't do to it).
As Alex rightly said, as the boat gets bigger, so does the cost of maintenance and ownership. A 25-28' is a great option, and a good way to "test the waters" to see if you enjoy boat ownership.
Another thing to consider is where you'll keep her. There is a guy on the C25 owner's site who keeps his boat near the 14th street bridge. GREAT location. I wish I had given that more consideration when I lived down there - I really missed getting out on the water. Ocaquan (sp?) and Solomons are also interesting options, depending on whether you live in the District, MD, or VA.
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