I've towed 5500 lbs with my '95 roughly 50 miles on multiple occasions. I also drug a 4000 lb popup camper all over New England for a two week vacation. Since then I've added a newer Durango and towed a 7k lb camper out to Yellowstone and back. Just to give a little background...
The 5500lb load was all weight, very little additional wind resistance. M1102 trailer. Speed kept to 60 mph tops, most of the time 50 mph. Surge brakes on that trailer. Truck was running 37" tires, ABS and LSPV removed, upgraded brake pads front and rear (Hawk LTS pads). And airbags in the rear springs.
Power was very lacking, handling was ok. Braking was ok. Wouldn't want to drive it much further than I did.
The 4000 lb popup was a dual axle, electric brake. The truck was set up as described above. I did have an electric brake controller installed. It was fine up to 50 mph power wise, braking was fine, handling was fine. The popup had a bit more wind resistance than the military trailer. Above 50mph, you could feel it. I ran the highways a decent amount on that trip, and spent a lot of time in 2nd and third. Frankly, I flogged the truck for two weeks.
Just for comparison, 2015 Durango with the Hemi and tow package. 30' travel trailer, 7k lbs loaded. Weight distribution hitch. A lot of folks would say too much trailer for the truck, but all my numbers were in acceptable ranges, except for tongue weight. That rig towed so much better, handled better, braked better than anything I have pulled with the 80.
If you are going to swap out the drive train, then power will be a non-issue. A weight distribution hitch makes towing so much nicer, I highly recommend using one. Problem is Toyota was very specific not to use one. My theory on this is the brakes. The LSPV require the back end of the truck to sag in order to up the pressure to the rear brakes. If you use a weight distribution hitch, that doesn't happen. Personally, I would yank the LSPV and ABS to allow the use of a weight distribution hitch. The brakes on these beasts can be more than adequate for this job. The weight distribution hitch is a superior solution to airbags in the springs.