I run transmission cooler with electric fan installed after the factory cooler. Running down the road in TC lock up it never comes on. a long hard crawl up the mountain it runs a lot. Also installed transmission oil temp guage in the cab so I know what's going on. If you're going to install a transmission cooler get one with a fan on it. If you're towing up a long bumpy dirt road you won't have enough air flowing over your coolers to do as much good. I'd wire in a small LED light (spot for it on the fan) so you know when it's kicking in and out if you don't have a trans oil temp guage.
I got something like this
http://www.etrailer.com/Transmission-Coolers/Derale/D13960.html
I haul lot's of hay and equipment on a gooseneck and bumper pull stock trailer.