DD,
I'm more or less in same boat as you with a need to occasional short haul 200 mi, tractor and accessories, to date biggest haul 18,700 GVWR pulling 9T capable GN dovetail trailer (top of the line new everything dual axle trlr).
I upgraded my truck springs www.activesuspension.com also hi perf shoes/pads and cross drilled rotors, 30K rated strong GN hitch Putnam Lock & Load www.putnamhitch.com, and best brake controller I think on the market Prodigy. Uprated tires and rims to 3300lb rating, have a backhoe I'll need to move as well I have some more mods to finish before that pull.
I'm way over factory rating, but am not a factory truck anymore and know legal risks but I also keep eye open, run with a escort and CB to know what is going on ahead mitigating risk as best I can. No real grades to speak of mostly rural low speed driving.
Upgrade your cooling to 97+ config., I had HD clutches added to my L480, remote trans electric cooler, and deep aluminum finned trans pan, just added new Hp injectors, and soon to be dual parrallel fuel pumps.
I feel I'm falling short on fuel delivery with a big load press to IP falls to 2 psi from 4 and engine not up to full potential for want of more fuel.
I also think dual oil filts a good idea aid in cooling some, as there is extra oil to be heated and passive cooling on oil filt bodies no longer beside the engine.
Tim, 98GM K1500 6.5TD(L56/L65), Heath PCM,3.73 gear,4L80 tr,4" exh,Amz air filt&dual oil flts, Heath remote FSD, TDO-7 clone turbo, Heath fan clutch,mandrel crossover, pilar gage BST/EGT/TRN, remote elec fan tran cool,alum trn pan