IMO the first thing you need are Disc brakes on the front. I've never cared for the 1/2 tons lack of brakes. That's not saying you can't take it easy, keep an eye down the road and compensate. In an emergency 1/2 ton brakes are way inadequate.
You don't say what the trailer weighs.
The towing I've done has been with a 1963 3/4 ton, and a tired 292. I've towed more than a few old trucks on a trailer with it, not to mention the big cab over camper, but not both. Never had a problem with the 292, yes it could use more power. Worse case was dropping the granny box into third and running about 35 mph for 10 miles up a grade.
Larry
