Those are some big boats to be towing with the VX, especially the sailboat. I've towed a small enclosed camper with a Wrangler (same short wheelbase, high profile). In downtown Chicago traffic, the trailer started wagging me back and forth like a dog with a squeaky toy. The front end would go back and forth with all the weight coming off the suspension at each side. Unnerving as hell. I found that the only way to stop this, was to actuate the trailer brakes and apply the gas at the same time. Once I figured out that trick, I never had any issues. Still, not a preferred situation.

I think a small boat, a couple jet skis, atv's, or dirtbikes, a light sport aircraft, or a utility trailer or pop-up camper would be what I would be most comfortable towing. Anything above 1,500lbs, I'd want a trailer with brakes. I think it matters how often and how far you plan on towing that boat.

As far as messing with the TOD, you could install an off switch so you could tow in 2wd. Don't use it in 4th gear either, overdrive is not intended for towing, and you could easily burn out that tranny. Keep the speed down as well, and you'll be happy for the advise the first time you come to a stoplight.

Etisport, that's probably a bit much. I'd probably rent or borrow a truck for the day, or a utility trailer rather than an enclosed one. Besides all the extra weight, you have a lot of drag on an enclosed trailer.