choices
From the tone of your initial inquiry, I suspect you are talking about purchasing a used boat. In the 25 - 26 foot range there are a number of good trailerable boats out there, and many of those from the late 70s and 80s are still in good shape if they have been well maintained. Hunter, Catalina, O'Day, Ericson, MacGregor, and a few others all offer what you are looking for. Practical Sailor published a good reference book, "Practical Boat Buying", several years ago that assesses several of these boats. A centerboarder with built in ballast, rather than a swing keel (heavy keel means potential problems with the pin and ultimate stability if the keel is up) will allow you to self launch and recover from your trailer. You probably don't want a fixed keel boat that requires deeper launching. Instead of fixing your sights on one brand, look around for a decent deal. The MacGregors seem to be more lightly and cheaply built than the others named, but their owners seem to like them (see Richard's comments here). Condition of sails is a biggie that many first time buyers don't consider - have an experienced sailor evaluate the sails on any boat you are considering - blown out sails will mean you'll be spending upwards of $2k above the purchase price. Also, check to see that it can be towed by your vehicle, or that you have access to an appropriate truck, etc. Wander through a couple of marinas on weekends and talk to owners - most of them are glad to share their likes/dislikes about their own boats as well as others, and they might even know of a deal or two. As they say, don't fall in love with any particular boat until after the sale - there are lots out there in this size and if you are willing to wait a little while, you'll find a number of good deals.