We're looking at ~30 foot boats, mostly all from the 70s, $5,000 - $10,000. We currently have a 1982 O'Day 25 Centerboard.
We will be using the boat for daysailing and cruising either side of Long Island, the Hudson River, and Upper and Lower New York Bay, and hopefully a summer trip out to Martha's Vineyard.
We're looking at a 1975 Santana 30 and a 1979 Cape Dory Intrepid 9M that are similarly priced and both seem to be well maintained and turn-key. Also being considered are the Catalina 30, O'Day 30, Columbia 9.6, and the Grampian 30.
Here is what we don't like about our current O'Day 25:
1. floats like a cork at anchor, too light for anything but the best conditions
2. porti-potti & no stove
3. too slow, although we are not planning on racing (I race on other boats)