I do not plan on towing the Jeep. I have towed the airplane trailer with a street oriented Dodge 1500 with a 5.7 several times on the highway and country roads. I was actually really good. I want a short wheel base, short as possible truck too because I want to put a snow plow on it and need to be able to turn in tight places.
My vote would be Power Wagon. But you might run into some issues mounting a plow. In that case my second vote would be the 2500 outdoorsman with the 5.7 Hemi.