Hawk,
I'm excited for you! Picking out the perfect boat is almost like looking for a wife. Only the wife won't cost as much!
Here's OUR story. See if you can relate. (OK veteran readers, comence with the eye rolling)
October 2008, I asked my 16 year old son what he'd like to do, father-son activity, because as he was getting older, we did less together. He said "Sailing!" So, we cruised Craigslist for a month or so before breaking it to Mom. I'm guessing the body snatchers had stopped by earlier, because in November when I told her, she said it sounded great. Two weeks more cruising Craigslist, and we found Phoenix down in Mass. We bought her late November (ish).. We didn't have a trailer to move her . . . or a truck to pull her . . . and we didn't know how to sail! But, I'm not a complete moron. These issues were talked about BEFORE we signed the check! I found a dually trailer, raised the roller stantions and built a roller keel support. Then, one beautiful December day, we picker her up and hauled her 125 miles with a Dakota (3.9 ltr). She was fine the whole way, but I wouldn't do that again. We got her home and bundled up. The in January, Alex and I took sailing and seamanship classes from the Coast Guard Aux. at a local college.
We bought 2000 F150 (5.4 ltr) and trailered her to the water a dozen times last year.
The boat weighs 3400 lbs empty. Add 400 lbs in gear and motor, another 1500 for the trailer (I'm guessing). That's 5300 lbs. The package trailers like a dream. We travel about 6 miles to the put in at Saco Bay or 35 miles to Caso Bay, down the highway, through busy traffic, no problem. So, big is trailerable. But keep in mind; pulling something that long . . . you're almost as long as a semi-trailer. We are 49 feet from stem to stern.
I think the Mac 26 is water ballasted, isn't it? That will help. If you find something else, keep an eye on the draft. The term "shoal keel" is your friend. Ours drafts about 30". Also, an untimely word of wisdom: fall is a great time to buy a boat because folks would rather let it go cheaper than spend money on winter storage.
http://pages.sssnet.com/go2erie/wind02.htm
This link has list of boat specs that might help.
So, a newbie like myself, I hope some those many words will make you say "Oh, I hadn't thought of that!"
Drop me a private message if you're interested in some of the other things we've run into.
Don
Biddeford Maine