Diesel or gas?
-You probably would benefit from a larger cooler with that much trailer. But it is very possible to over-cool the 4R100, especially with the V10.
-If you have the V10, skip the 4.10s and go straight to 4.30s. That'll be a jump actually worth making. 4.10s with either motor will hardly be noticeable. With the diesel, I'd say stay with the 3.73, and use the $ to do some minor performance upgrades instead. A free flow muffler and larger air filter (biggest NAPA paper one that will fit) will do more than gearing in the diesel. But with the V10, gears are everything.