I had a 2001 Ford 10' box truck with a slightly extended rear bumper (~10") that I had a hitch put on and pulled my 24' 1968
Tradewind to Sturgis with. Very convenient. I would be concerned with a much larger box truck (I also have a Mack box truck). That would beat the AS to death, but the 1 ton box truck basically rode like my Chevy 2500 pickup. You will be fine as long as the hitch assembly is long enough for clearance in tight turns. You might want to consider airbags on the box truck along with the brake controller so you can level out your ride (depending on how heavy you load the box truck).