When are you going? If its tomorrow, never mind.......
But, if you have time, I would definitely put in a temp gauge. I would also try to work out a way to measure the temp coming out of the tranny.
The best way probably, would be to cut the transmission line between the tranny and the cooler, and put in a "T".
Plumb the temp sending unit into the "T", and then wrap it with insulation.
That way, even if its not in the direct fluid stream, the fitting and sending unit will quickly all reach the same temp, and will track the fluid temp pretty well.
Or, clamp the sending unit to the line, with some heat sink grease and then insulate the area.
It works with refrigeration expansion valve bulbs.
That will hopefully let you spot trouble in time to pull over and run it at fast idle in park until it cools down.
The other thing I would consider, is changing tires.
If you can find some rims and good smaller diameter tires, you can swap them and put your 33s in the towed vehicle to put on after the tow is over.
This will have the effect of changing the ratio and should let the transmission see less load, and easily stay in lock in OD.
Cheaper than gears.........
I used to have a set for my 3/4 ton Ford.
I had the 16.5/33s for hunting season, and a set of regular 16 inch wheels with Michelin radials street tread for the summer when I was using it for some towing and as a DD.
After I got the SUV, I just left the 33s on, and traded the others to a guy for a nice rifle.