I've done it, but I sure like my dually now. As long as it's not windy, I would think you would be fine, but I would make darn sure I had good tires on the pick up and trailer. A blowout with a dually is fairly manageable, with a srw, it can be a white knuckle experience, especially a rear tire. Front tire blow outs are about the same, dually to srw, but when you lose a rear on a srw, the trailer tries to push the pick up sideways like a power slide from the dukes of hazard. The cummins has plenty of power and brakes to handle the hills, and you do have an exhaust brake, right?