First.....I've never owned a MacGregor sailboat. I have rented Venture 17's for daysailing years ago.
I would never, ever consider owning a Mac 26M or X. I would, however, have no problem purchasing the older, D and S models. These older models, like sumner and ruth's 26s, have stood the test of time as excellent trailer sailors. (If you are lucky enough to find one as tricked out as Sum's... snap it up, pronto)
The M and X models are a completely different story. I was invited out on one a few years back..... the wind was about 10kts.... I was very uncomfortable, I couldn't wait to get off! (and I've been sailing 30plus years) Yes, there's lots of room inside, but that's it. The rigging is so lightweight, and the freeboard so high... oops.. I'll stop here, because most everyone has heard me rant on these boats.
If you're looking to get into sailing there are many, many adequate starter boats that are easy to trailer and maintain, and sail like a dream. The aforementioned 26s and d are good, so is the Cat22 and 25, the Hunters, ....
When newbies look at sailboats for the first time, they usually focus on a boat's interior and how shiny it is...... but if you're serious about giving sailing a try, do lots of research on what makes a good, starting sailboat. Learn to recognize the true condition, not just what's on the surface. Do not be prejudiced against a tiller steered sailboat.... a wheel is impractical on any boat under 30 ft.
Once you get educated, you'll learn that a boat's age isn't as important as its condition... so get cracking.