Model selection
There was no mention of trailering the boat anywhere. I have to assume that the intent will be to maintain a slip at a marina so that your time will be spent sailing instead of learning techcniques to quickly launch and retrieve the boat.There are countless boats that fall into your "wants" category. We went through the same process a couple of years ago. I wanted a non-water-ballasted boat rather than a water ballast model. We looked at Catalina and Hunter 22s, O'Day 25s, Catalina 25s and 27s, Hunter 25s, 25.5s and 27s, C&C 25s, 26s and 27s. And a lot more. All of these had great examples of features we thought important. We also saw a wide range of conditions (from major restoration projects to truly ready-to-sail well-maintained boats sailed weekly). We came very close to buying a very nice and well-maintained O'Day 25, but the cabin was just a little too cramped for the admiral. Similarly, it was only logistics that kept us out of a Catalina 25 fixed keel, but SWMBO (she who must be obeyed) would have thought it a bit small though would have enjoyed sailing a C25 (great sailing boat, large owner base, plenty of aftermarket support!). That was not the only C25 we looked at.In the end, we bought a Hunter 25.5. We got a reasonably good deal and its a lot bigger than boats of similar length (much bigger beam - 9+ feet - and about a foot longer than many other "25" foot models). The admiral was very satisfied with the cabin space and likes the way it sails. It was also located relatively close to where we wanted to sail (more important than you might think - transportation costs can be pretty high).Your mileage may vary.Rather than just considering a specific make and model of boat, another option might be to find a size and general price point that works for you. Look at places like http://www.yachtworld.com in the used boat listing to see what is out there in your size and price range. Find the right model that catches your eye. Also consider whether you want to invest your time in fixing up a boat with a few problems or if you would rather pay a little more and just go out sailing.Before you write your check, make sure you get an expert opinion on the candidate's condition. Surveys on boats in this size category are important to determine where there are major expenses ahead and also will help you determine the cost of ownership after the deal is done.