I think one of the bigger problems is knowledge. I know too much about towing now, so what I might have done in the past, I won't do now.
My Subaru had a max tow capacity of either 2000 or 2400 pounds, depending on where you look. And the 1 1/4" hitch has a max load of 200 pounds. So when I look at the little 192, with a theoretical displacement of 1400 pounds, and factor the trailer and all the junk I have put ON the boat, I'm right at my max limit. So I'm ok pulling the boat out and putting it in, towing maybe 15 miles to my friend's house for working on it, and stuff, but I'm not comfortable towing 2 hours down to the Chesapeake, which I'd really like to do. Even if I put a transmission cooler on the car...
That being said, I have "towed" a 222. Our friend has a lift and centerboard pit, and I had the boat over for pendant replacement. While I was there, he asked if I could move our other friend's 222 from the cul de sac to the driveway. What, a few hundred flat yards? OK. HOLY COW, was the tongue weight on the 222 heavy! I could really feel it lower the back of the car. But, yeah, I'm surely not going to be towing a 222.
In looking at bigger vehicles, such as the Honda Pilot, Nissan Pathfinder, even the Ford Escape, they all seem to have low tow capacities if you have a 4 cylinder motor (even as low as 1500# in some cases.) But if you have the V-6, it jumps to 4500# or better. I'm guessing this is a function of the V-6 getting a beefier transmission no matter front or 4 wheel drive.
Ugh. I bought the Subaru 2 years ago to be able to tow my Harpoon. Then dontcha know, I had it for a year and I had to go off and buy yet a bigger boat that needs more tow capacity. My vehicle choices have not had good timing or scalability...
Brian