I tow with my 2003 Dodge Ram 1500 Crew Cab with the Hemi, offroad package, and 3.92 gears. I've also reprogrammed the truck with a Superchips programmer. (Towing mode) Only issues I've had is long hill climbs. I slow down to about 25-35 mph. I just let it do it's thing and don't push it. The only time I had transmission cooling problems is when I was towing a 7100 lb bobcat and floored it to "see what it can do." Don't do that, it's not worth it.
I pull my XJ and have pulled a Bobcat on tracks, a 3/4 ton suburban and a chevy C20 on tons. My trailer is a 5 ton Hudson weighing in at 2,000 pounds. When pulling the XJ my trailer weight is around 6500 lbs.
Because it is a half ton and the suspension isn't up to par, I run a weight distribution hitch. This helps tremendously, but if you don't have the cash for a WD hitch then pay close attention to where you load your vehicles on your trailer. You can find the sweet spot so that the rear of the truck doesn't sag too much while having minimal sway on the trailer.
Also, get a brake controller and make sure your trailer has brakes. It makes a world of difference and now that I went that route I never want another trailer without brakes. I run the Tekonsha P3 brake controller. Very nice and easy to install.
