just my .02 but.... I pull my tractor (and a lot of other stuff) w/ a 3/4 ton Chevy. For my money (and piece of mind) the bigger brakes, heavier suspension are worth it. I would also seriously think about a goose neck hookup. They pull easier, back easier (IMHO), and distribute weight on the truck better. Put the ball a bit in front of the rear axle and you put weight on the front axle instead of levering it up like with a bumper hitch. More $$$ up front, but lots safer IMHO. I have had goose necks in 1/2 ton trucks as well and the sway is not near as bad. A trailer attached to a bumper has a lot of leverage on your truck and the softer suspension of a 1/2 ton can't absorb as much sway. Also, you didn't mention if either trailer had brakes. They sure do help keep the trailer behind you. If you depend on the truck to do all the stopping the trailer can push you places you do not want to go. Also, w/ trailer brakes if you start to sway, you can tap the trailer brakes a little to bring it back in line. Handy for hills also.
Also, be careful unhooking w/ the trailer loaded, most trailer jacks really aren't rated to handle the load, much less be stable enough. I have folded a couple of jacks that way.
Also, be careful unhooking w/ the trailer loaded, most trailer jacks really aren't rated to handle the load, much less be stable enough. I have folded a couple of jacks that way.