Re: Would you tow this with this?
Been a Jeep driver for more years than I care to count and I've towed things with Cherokees most people wouldn't tow with full size trucks. Your main problem is stopping. Most Jeeps have notoriously small brakes for the vehicle weight. Throw a trailer on top and you could have a pretty tough situation, quick. Though you might have taken care of that with the disks and trailer brakes. For that distance/speed, I'd never hesitate and let's get to the water. But, if you're going to go any further/faster, you might want to look into something that has better stopping power. Yes, everyone says short wheel base is horrible to tow with. But, that short wheel base is what makes it so you can put that boat in the garage with 3 inches to spare. There's a LOT to be said for the shorter wheel base of a Jeep when you need it. Also, most Jeeps have a very tight turning radius. That helps a lot.
I tow a 21' Answer on a dual axle trailer with a 92 Cherokee. Check my signature and you'll see, it's NOT a small boat. My trailer doesn't have brakes yet. Just anticipate your stops and drive for the other guys.
Just yesterday, I put a hitch on my Hyundai Sante Fe, another short wheel base vehicle. We'll see how that one works next weekend.
Yes, eventually there will be brakes on the trailer or a new trailer with brakes.
And, knock on wood, I've NEVER had a Jeep stuck but I sure have pulled out a bunch of other vehicles. Including Broncos. And Chevies. And Dodges. And Toyotas. I keep telling my kids, both of which have Wranglers, that I'm going to put little Chevy/Toy/Ford stickers on the side windows, just like the old fighter pilots did when they shot someone down, when I pull someone out.
BTW, Jeeps are the official recovery vehicle for EVERYONE.