I recently towed a 16' Scamp trailer to the Melt, some 650 miles away. It was hot, I had the camper little weighty (~2500#), 4 passengers and a dog. I suggest that he keep the trans out of OD. I got the tranny a little hot on the way there. It cooled off enough and didn't have a problem. On the way back, I got the tranny hot again and basically toasted the fluid. I did a fluid change 2 days later, but it was more of just empty the tranny pan. I'm getting ready to empty it once again as well as empty the torque converter.
If you can, add an extra tranny cooler in-line with the return line of the tranny. The little stock unit in the radiator is not enough. Keep the tranny out of OD and keep your speed down. I didn't have brakes on my trailer and it didn't really feel it. At gas fillups, check tranny and oil.