Yeah, if you are thinking about "keeping cool" focus on cooling system. Fluids are way better at transferring energy, in this case, heat from a thermodynamic perspective than air.
Where an air-cooled engine would be better than water-cooled would be simplicity. That's it. I mean, you don't have a VW Beetle under your hood, right?
If you have the towing option from the factory, then you have engine oil cooler, transmission cooler and power steering cooler. If not, then add those.
These GMT 400s worked/work very well for towing and hauling. About the only improvement I can think of is using a 7.4 radiator, as that was thicker.
Maybe compare cooling system to 3500HDs GMT 400. Those trucks were like GVWR of 15,000 lbs, and a lot of them were equipped with 5.7s.
Put some new coolant and inspect hoses and check thermostat/radiator.