I used to tow a bunch with a 1/2 ton Chevy of that gen. The best thing you can do for your brakes is swap to Hawk Superduty pads....Reybestos made a great pad to but I can't remember exactly which one-I just know it wasn't something you could just go buy at the parts store.
This will be better than any rotor, caliper, or brake line change. I felt it was absolutely required with the towing I was doing. Parts store pads-no matter how expensive, just don't come close.
I would put a transmission temperature gauge on it too, just to help keep an eye on things. FWIW though, I NEVER had a problem with the 4L60E. Towing about 6K plus, including in towns etc.
One other thing. Look up BlackBear tune. If they are still open I would talk to them. The handheld tuners are garbage and these guys get lots of good reviews. That is with the Vortec trucks. Not sure if they have experience with the TBI trucks, (and not sure which one you have, I would have to go back and re-read to double check)