Does your DIC have tranny temp? If so, I would just monitor your everyday temps vs those while towing and parking the trailer.
If you see something that alarms you then add a cooler and or fan.
I once added a fan to a second aux cooler on a 94 Caprice Wagon. I didn't go with the thermostat but instead directly wired it with a switch on the dash that I then could turn the fan on and off myself when I wanted to. While it did help, it didn't drop my tranny temps like I was anticipating it would. I added the fan to help with tranny temps in stop and go traffic.