Should not be the trans
If he has an ATS or other upgraded transmission then he should be towing with the TC locked. With the TC locked there is very little heat created by the trans, and therefore adding an additional or larger trans cooler will have no effect on the engine temps.
If by chance he is pulling with the TC unlocked, then tell him to lock it!! That is how the upgraded trans' are meant to be used. Also is this overheating when on the freeway, or when negotiating slow twisting roads where he might not be using Lock on the TC??
The most probable cause of heating is the radiator pluged with dead bugs, leaves, and dirt. Make sure the outside of the radiator and A/C condernser are clean, this often the problem.
Other wise, make sure the fan clutch is engaging when the temp guage gets to about 200* there is no mistaking the fan engaging, it sounds like a jet ariplane just passed over the truck.
Hope this helps, Greg L