Some considerations
We went through the same thing you are a couple of years ago. I wanted an easy to handle, affordable boat with a big cockpit. My wife was more concerned that the head be in a separate compartment. It came down to a choice between three boats: the Catalina 22, Catalina 25, and the O'Day 23. We bought the O'Day for two big reasons: the separate head compartment and the keel/centerboard configuration. After sailing her for two seasons, I have come to a couple of conclusions: I agree with my wife that the separate head has made a big difference; it really provides necessary privacy, especially when sailing with other adults; the keel/centerboard configuration is more stable and less maintenance than the swing keel of the Catalina 22; and a fin keel boat is significantly more stable than both.If you are going to trailer your boat, you really need a swing keel or centerboard. I agree with the previous writers that a Catalina boat is well made, stable and will hold its value; however, I think the Catalina is not as good a boat as the O'Day 23. The O'Day is heavier, more stable and roomier below. The Catalina however might have a pop top (a truly great option), can be supported by the manufacturer, and is simply the most popular production sailboat ever.If you are not going to trailer the boat and you expect the seas to kick up with greater than 3 or 4 foot waves often, then I would urge you to consider a fin keel boat. They really are more stable, sail flatter and point higher than any centerboard-type boat. I really liked the old Catalina 25 fin keel model. It is small enough to be easily handled, is large enough for real weekend or short cruising, is stable and sails really nicely. In Conn., C-25's are available from around $6000-$12,000, depending on age and condition. Be sure you look at pop-top models.