I own a 1996 MacGregor 26X, and I would concur with most of what David Dennis wrote.
I have about 155 hours of sailing time in the boat at this point, most of it in light air, which is what one mostly gets on Lake St. Clair where I do most of my sailing. I have also sailed the boat on Chesapeake Bay and Lake Michigan.
I have had the boat out in two situations where the wind was over 20 knots, gusting to 30+. The first time I was pretty frightened, due to my own inexperience, but the boat performed properly. I got her reefed, she handled well under reef, she forgave me my mistakes, and nothing broke. The second time I was a little braver; I kept the sails up for a while and had some real fun, but then furled the jib and sailed her like a cat boat back to harbor. Again, she handled properly and nothing broke. I've had the outboard break, and my VHF break, but what MacGregor sold me hasn't broken yet.
Because of the unusual way the boat is engineered, you have to think about what you're doing. The reason some owners damage the rudders is that they leave them down while powering at high speed. You're not supposed to do that. The rudders are for sailing and slow-speed powering, as in maneuvering around a marina. High-speed powering is done with the rudders and centerboard UP.
It is always tempting to leave the ballast out, especially when you think the wind will be light. You can do it and get away with it--I often do--but again, you must think about it, and keep your eye on the weather, and be ready to load ballast when necessary. You must also be aware that you use the boat either with full ballast, or none; you DON'T use the boat with the ballast half-full!
Dry-sailing the boat is possible. I did that for the first season I had mine. The mast and such is not as quick to rig as MacGregor makes out. If you did it purely for speed, you could probably get it down to 15 minutes or so, but what if, in your haste, you forget something important? The result could wreck your rig. So you take a half-hour to 45 minutes and you do it RIGHT, carefully checking everything as you go. I'm basically a lazy person, so I like having my boat in the water all the time, but I still have plans to trailer-sail her a number of places. Having the option to trailer-sail the boat, while also having a big enough boat to do short-run cruising on, makes the boat perfect for me. What works for me when trailer-sailing is to go someplace on a schedule that puts me there on Thursday or Friday. I get the boat in the water and in a slip the day I arrive, then relax overnight, sail for a day or two, then take the boat back out of the water on the last day and go home. Trailering, rigging, launching, sailing, retrieving, unrigging, and trailering again all in one day is just too much like work for me.
You will not find that the boat is about fit-and-finish. There is no wood aboard. Storage space is also a problem. There's a lot of room under the seats and stuff, but you have to pick up some plastic storage bins (I got several 5 gallon Rubbermaid boxes) or some other expedient to keep what you put in there dry, as it's all essentially in the bilge. However, I must say this is the driest boat I've ever been on. The only time I ever have water in the bilge is when I put it there.
Yes, you have the potential of six berths; no, there's no place for six people to put their stuff and still sleep, unless they put it all out on deck all night. Yes, there's an enclosed head; however, if you're more than 5'10", you'll find it difficult to manuever in there.
Can the boat be cruised offshore? The dealer I bought mine from took his family with him, trailered the boat to Florida, cruised the Bahamas, and brought it back without incident. On the other hand, he didn't encounter a hurricane in it.
When we shopped in 1996, the competition was the Hunder 23.5, the Compac 23/3, and the Catalina 250. When we got into the MacGregor the first time, the extra space, excellent cabin layout, ease of launch, and price made us buyers very quickly. We haven't regretted it for a minute.
Living where I am, I can hardly believe that MacGregor has essentially no dealership representation in Michigan. There's a part-timer in Grand Haven who sells from his home and a place in Otisville that can't even demo the boat on the water. When I used to take the boat to a launch ramp, I swear I could have sold a dozen of them right off the trailer.
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Robert Bethune
Freshwater Seas
Ann Arbor, MI