I went with the 255s for lots of reasons. Larger than 265s, lighter than 285s, better traction in most situations than both.
No trimming/rubbing and yes I'll do it again if they ever wear out.
Great tires with great traction (only set of MTs I've owned). I only run them when going off road.
Most of the time I run the stock 245/75/16 Dungflops which will be replaced by 265/75/16 Dynapros when they wear out.
I'm currently waiting on a full set of Relentless skids & hybrid sliders with 2 piece kickout. Good thing I'm so busy with the new house it makes the wait easier when you don't have time to go wheelin.