Just my .02...
I pulled my '87 T on a heavy trailer with my '97 F150, which had the 210HP 4.2 V-6/automatic. Did this about 10 times, from my place to Norwalk (~200 miles round-trip). Acceleration wasn't great, and the bed sagged some, but once I had it up to speed, it would pull at 80-90, no problem. I did invest the ~$200 in a
weight-distributing hitch, which helped out immensely, and I HIGHLY recommend it. If you tow once without it, then install one...you'll immediately know what I'm talking about.
NOTE: The key is in how you allow the transmission to shift. While towing with a lighter-duty truck/drivetrain, ALWAYS keep the truck in
third gear (1:1)....NOT overdrive. Yes, you'll be sailing down the highway at a higher RPM than you're used to, but bear in mind that the SHIFTING is what will kill your automatic transmission when towing. The added engine speed won't hurt anything; it will just diminish your mileage slightly, and it will keep the trans line pressure up. You'll also find that keeping the V-6 in the fat part of its power curve will allow greater control of the load, especially when passing.
Since your truck has the trailering package, be SURE to use the tow/haul mode 100% of the time, while the trailer's attached. This will up the line pressure, and raise the shift points.
...and of course, make sure you invest in a decent
brake controller for the trailer's brakes. A good unit is less than $100.
BTW, I now have a 2000 GMC 2500 4x4 Extended-Cab, Long Bed, with the 6.0 LS1 V-8. No more problems in the towing department.