Currently the owner of a 92 D250 Cummins with automatic and former owner of a 11 1500 Crew cab I can offer some insight.

Short version, the 11 tows faster but the 92 is much more stable.

Long version, both trucks are factory rated for a 12000 gcvw. The 92 is transmission limited by the factory but manual trans trucks were rated as high as 17000 gcvw. Both have 3.54 gearing. Both are between 5500 and 6000 lbs empty so up to a 6500# trailer.

Trailer in this case is either a 28' camper or an 18' car hauler.
Clearly the horsepower advantage is with the 11, much more nimble in traffic and merging, maintaining speed on hills better. But it just felt so unstable even with sway control and weight distribution. Non tow mirrors sucked too.

The 92 took more forethought into merging and plan on staying in the slow lane on hills. But the mirrors are much better (standard tow mirrors not giant west coast) and the whole rig just feels more stable, even without sway control or distribution.

These are comparisons based on making the same trip several times with each truck.

We sold the 11.