Since you are looking at 20 year old boats (give or take a few years), IMHO, how the boat is maintained is just as important as who the builder / designer were.
For example, I would rather have a well maintained Catalina 30 over a poorly maintained Tartan 30.
In 2004 I was in the same position as you - looking for a 28 - 32' racer / cruiser for day sails and the occassional over night / weekend trip. My sailing area is the Long Island sound - similar to yours. My budget was around 20K, again similar to yours.
My ideal boat (for me and my requirements) was a Catalina 30. However, good ones were too much money. I looked at many boats, including S2 (9.2A) , O'day (28, 30, 31), Irwin (30, 31), Islander (Bahama 30), C&C (29, 30), Hunter (30, 31, 34), Ericson (28), Newport, and a few others.
Again, IMHO, there was not that much difference between the boats. To me, the Irwins were not well made, I did not like the Hunters either so I took both of those off my list. I heard good things about S2, and I looked at 5 of them. All had bad leaks around the chainplates and as a result had wet areas and moldy, mildewed interiors. So I took the S2 off my list as well.
The O'day boats were nice but I didn't like the teak toe rail. I also didn't find a great one.
I was at one boat yard looking at an S2 (which was in poor condition) so I asked the broker what else he had that I could look at. The next boat over was a 1986 Newport 28. I went aboard and was impressed. All the creature comforts I wanted (hot + cold pressure water, head w/shower, galley, berths for five), plus the sailing and boat parts I wanted (diesel inboard, wheel steering, self tailing winches, cabin top mounted traveler, lines led aft, etc.). Size wise it was definitely smaller than a Catalina 30, but big enough for my family of 5 (3 young kids). Compared to the Catalina the Newport had a nicer interior with teak and holly sole, padded head liner, teak faced cabinets, etc.
The best news was that it was cheap. I ended up buying it for $15K with decent sails (including an almost new asymmetric sprinnaker with dousing sock), autopilot, etc. I enjoyed that boat for 3 years. In the fall I moved up to an O'day 35 and sold the Newport a month ago.
So, to conclude, you should consider Newport (28 and 30) and O'day (28, 30, 31) as well. You may be surprised. I'm sure you can buy very nice Newports for $15 - 20K. Same thing for O'day.
Deep Blue C, 2002 C&C 110
Mt. Sinai, NY
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