I have a tracked jeep that I've been fighting tranny temp issues with. Working through that I've dug into the problem quite a bit; in my scenario I couldn't get enough air flow due to the slow ground speed and had to add an aux cooler to cover the differential between my need and the factory setup.
Anyway,
Hot tranny's = dead tranny's; you want to keep the temp within manufacturer operating temps as much as possible. If your torque converter is not locked up you will generate a ton of heat; even with the tow/haul option dropping out of overdrive can help reduce temps (some tranny's do not lock up in OD). Staying around 200 degrees is a happy place, bumping up against the manufacturer limp mode limit is going to take a lot of life out of the tranny.
Aux coolers make a significant difference; the trick is to get a large enough btu rating to cover the need. On my jeep I was able to go from 270+ and climbing to staying under 200 regardless of the load.