I have double towed only a short distance no more then 50 miles at the most and only on two lane roads .that with a dodge ¾ ton 31foot travel trailer and a 19foot boat trailer behind the travel trailer that total about a 70feet rig . but I would not try it on long trips so what I thinking about building ramps for the bed of the truck mounting a winch on the headack rack to load and unload the boat and trailer off the truck. The boat is a 15’x60” john boat so the boat is not that heavy . Im going to start welding up the ramps next week will post pictures of it when I get it built .john