Sorry to disagree but a trans temp gauge is a waste of money. I do not believe It will give an indication that is actually useful. The OP should have noticed that before he started burping fluid, he was overheating. Overheating is a sure sign extra heat is being dumped into the radiator and they system is unable to normalize it.
One should tow in 3rd, not OD, and not tow anything with a total weight of 5K lbs (assuming he has a class 3 hitch). Also the tongue weight can not exceed the rating of the hitch. And seeing as Muddeprived baked his transmission fluid, he should change it.
Though I have occasionally pulled an XJ behind me, the XJ was never intended as a tow vehicle, but to occasionally tow the family boat around.
Adding a transmission cooler can extend the life of the transmission by keeping things a bit cooler, but if you are torturing the machine by towing in the wrong gear, insisting on doing 75 with a full load, or jack rabbit starts, you will fry your transmission regardless of what the tranny temp gauge says.
Just my 2C FWIW. Proper operation of your vehicle is the key, and in the time of the internet, failing to research your tow ratings and tow operation before setting off on an adventure is... well, there is no excuse for it.
-Ron