I've pulled a loaded trailer behind my '55 1st 1/2-ton. I have a GMC 270, an SM420 and 3.08 rear gears.
Pulling the trailer empty wasn't bad. Once it was loaded it was working the truck pretty hard to achive highway speed and really wasn't comfortable.
You don't say if its a 1/2- or 3/4-ton. In either case I would not count on the stock brakes to be adequate to the job, even with brakes on the trailer. If it were me I'd be thinking brake upgrade and a V-8 if I were going to use it for towing.
