For what it's worth, I pull a 28' camper (#6500 empty) with my '66 Custom Camper with a 327, 3 speed while utilizing a weight distribution hitch.
A little under powered, but the biggest concern is that the trailer literally pushes the truck all around even on a calm day. On a windy day with traffic passing me on the highway it's white knuckle driving. Drum brakes all the way around make for a little pucker factor too in an emergency stop situation. Therefore, we only use the truck for shorter trips.