We bought our 1993 Mac 26S (swing keel) last year. We LOVE it! I was surprised how well it sailed after reading different opinions on them. That might be because people get the newer 26X and 26M models (With 50hp engines) mixed up with the more traditional "Classic" models (Production on the 26S I think ended 1995...last of the classic models). BUT I never have been on a 26X or M so I can't honestly say what they are like, the pictures of the cabins look huge and Hunter boats has recently come out with a boat such as this, so there might be something to it. Anyway ours suits us, it's GREAT for a couple and sometimes some guests. I would't do more than daysail with guests but my Wife and myself love to weekend on it, we plan to do a vacation on it just bumming around the bay in September. The boats are not as cheaply built as you will hear, they are designed for inland bays, lakes, close coastal and such so they are not rigged like an off shore cruiser. It might not suit all but we're happy. Like many have said it makes a good entry boat and many people are content simply staying with it. We bought ours knowing we are going to move up, but we are happy learning what's out there, talking to other boat owners, and in a few years will move up to a larger boat, but now we're happily sailing in our "Nauti Time" and in no rush.
Our boat DOES seem to leave the marina many more times than the vast majority of our neighbors.
For other trailerable boats you might want to check out this site...The Trailer Sailor - Discussion Forums
It has gobs of information on many trailer sailors.