... Unless you want to trailer your boat... Not something I know anything, or care about.
Firstly, I concur with everything Eric has posted. I happily and proudly sail a 2001 26X and share all of Eric's appreciations for its shallow draft, large cabin, big outboard, etc.
As for trailering, I can perhaps add a bit to what Eric has otherwise covered very well. Trailering opens up so many opportunities that would not be available otherwise. We've towed ours to many lakes in Texas, Arkansas, and all the way from Texas to Florida to sail the Atlantic coast around Cocoa Beach, as well as some nice lakes in Central Florida, including motoring along the Saint Johns River, etc. And all in comfort, and with a familiar boat, and very cheaply.
Not to mention that we have often used the boat as a camper, staying in a campground, just like an RV, even on trips that included no boating whatsoever.
And while we primarily sail, and consider it a sailboat, our kids *love* tubing and wakeboarding behind it, even though it's not a speedboat, and it adds yet another fun activity to an already fun filled trip.
We love our 26X so much, that when we recently moved from Texas to Finland last Fall, we took it with us! and we are eagerly looking forward to sailing the Baltic and Finnish archepelego as soon as the ice melts -- for which the boat is absolutely ideal, given the boat's shallow draft and the nature of the rocky coastlines. And even better, we'll be able to just trailer it down to the Med, or over to Norway, or inland to the Saimaa Lake region, etc. And can spend a month motoring the canals of France and Germany, etc. etc. etc. etc.
The range of possibilities this boat offers is amazing. In a word *versatility*.
No, it's not a racer. No it's not full of teak. No it doesn't have an inch thick hull. No it's not an offshore boat. Blah blah blah. But it's a decent boat, for an affordable price, when fairly evaluated, and as with Eric, I know of no other boat that could possibly allow us to sail as often, in as many places, in as much comfort than our MacGregor. I've looked. I'm always one to upgrade to something else that better meets our needs or better fits our dreams. I've not found anything that, for the price (which for many of us is not a small deal), comes close.
I often dream of a bigger, better, faster, ocean capable boat that I can sail around the world and have no illusions about the limitations and quirks of my MacGregor, but I think that those who "talk trash" about MacGregors simply "don't get it".
So when you folks with bigger, better, faster, prettier, ... boats are stuck in a particular spot, and having to either spend weeks getting somewhere different or charter an unfamiliar boat to get a change of pace, we'll be enjoying our familiar and capable boat, which we know how to sail well and know every bolt and line, and we'll be sailing in more varied locations in the course of a year than most do in a decade, if not a lifetime.
It's something you either "get", or you don't. Other MacGregor owners will know what I mean.