In the end, that is the right choice.

 

I towed my offroad trailer on a 6000km round trip a few years ago. I has 3.21 gears in my two door and the trailer was 800lbs dry. The jeep did fine and that was the 3.8 too. Used the gears lots.

 

Just returned from a trip towing a 3k lb trailer about 500 miles R/T.

JKU Automatic, with tow package (NOT Max tow) and 3.21 gears. Jeep site rates this rig at 350 tongue weight and 3500 capacity.

Used weight distro hitch and sway controller.

Towed fine. Only issue I noticed was when pulling up steep grade, fully loaded with AC running, temp started to creep up. Had an 07 jku and temp did not rise under similar loads?

 

I don't think you'd have a problem. Trackers are aluminum, as is my 21' lake sport with a 150 v6 sitting on the back. I tow that thing no problem wherever I want with my 2012, 2 dr, 3:21.

My dad towed it 400 r/t on highways, interstates and twisties in his 2011 4dr auto just a couple weeks ago, and before that he tows his 19' centerconsole (fiberglass / heavy) on 750 r/t at least 4 times a year.

Run it before your trip to get the gas tank on the boat close to empty, as fuel definitely contributes to the weight.