Originally Posted by russ1436
I don't think the issue is gearing or power. The issue is wheel base. Because the jeep is short it's not stable pulling weight and could jackknife when trying to stop.
True on the lackknife comment, but actually most of the issue IS gearing and power. With the relatively light boat you're talking about getting, you won't have a jackknife problem even with the 2-door and no trailer brakes. I know this from actual experience.
No doubt, your jeep is going to be a dog towing that load. I tow a 17ft fiberglass runabout with a 4cyl 3.0L I/O. Basically the lightest runabout you can imagine. My jeep is a 2010 6sp manual 2-door w/3.73 gears and towing package. And it's a dog, especially when it's 90 degrees out and the engine has trouble making power. Yours will be worse with 3.21's. You'll be OK. You won't hurt your Jeep. But it's really only good for the one mile to the launch.