I tow anywhere from 6,000 -10,000 lb trailers on a weekly and some times daily basis. I of course have changed to the Nv4500 5 speed, 14 bolt SF, Air Bags, 12,000 lb hitch, 10pr tires and trailer brake controller. I am still running my original L31 with 340,000 mi on it. Your biggest problem is the short wheelbase of your tow rig and being able to control your trailer in windy conditions, rough roads and stopping.
You will Definitively need a larger tranny cooler if you tow very much weight in the hills. Before I changed to the 5 speed, I towed a 20' toy hauler from Las Vegas to Redding, Ca (12 hr drive). At the time I had a well built 4l60E with large pan, transmission temp gauge and stock trans cooler. I ran in third gear the entire time and watched the temp get scary hot a couple times.