Make sure it's an all ALUMINUM trailer, stick to flat terrain and you'll probably be okay. I pulled a 16' stock trailer with two bulls around 1,800 lbs each with a '96 5.2L (318 cu in) 4x2 Dodge 1/2 ton for a little over a year.
Yeah, I blew the tranny, but that had happened a couple times before, so I write off the cause being Dodge's crummy 46RE automatic transmission, which isn't known for reliability. If ya think you're safe with the Dodge 5.9L (360 cu in) engine, you're not, they use the 46RE on those models too. Ya gotta get the V10 or the Cummins to get the "good" automatic tranny (47RE). I now have a '01 Dodge 1/2 ton with the same engine and tranny - I never tow with it, just drive it to work and back. But funny enough it's been in the transmission shop just as much. Go figure.
Back home, we pulled a 16' loaded stock trailer ever now and then with a 1990 Ford Ranger (with the rare, BIG 4.0L V6). But not very far - only down the road and back. And the transmission eventually blew in that truck as well. Not to mention the shocks.
If the road's the slightest bit hilly (even down here in Florida sometimes - like when going over an overpass), make sure you use your "overdrive off" or "tow/haul" button. Constant shifting between gears will tear up your transmission right quick.
Also, bear in mind if ya have 4x4, the rated towing capacity is less (because of the extra weight of the front drivetrain). I wouldn't try using the 4WD while towing a loaded trailer - the front differential probably isn't up to the strain.
Mike Bishop -
http://www.flbullrider.com