I can't speak for the newer 5.7's. My FIL had an '03 2500 with the 5.7, manual said run '87 minimum.
I had my 6.4, and I ran it for 3-4 years on '91/92 (depended on what station I was at, my '17 manual said run '89 minimum but that stuff SITS in the tanks around here so no telling how old/degraded it is) and it ran great. Switching to '87 when they jumped the price of premium but left regular alone (price differential is now something like $1.25 here, more at some stations), I saw no loss in mileage or power, and no noticeable knocking, so I'm sure the computer compensated for it. The first few tows of the camper I switched back to premium, then I forgot a couple times and still saw no issues towing with '87, even on 3-4 hour (250-350 mile) hauls at 65 mph. I also saw no real difference in mileage while pulling on the two different grades of gasoline.
If I were going to be pulling >50% of the time with a gas motor, yes, premium (91/92 octane) would be the way to go, just for added peace of mind if nothing else. For the occasional haul, I would say it's up to you. I personally had no issues but that doesn't mean you won't, though it also doesn't mean you will.