Before I got the 285 series ST Maxx on the Tundra, I ran through 2 sets of ST's in the 255/85/16s. The first set went 50,000 miles and the second set went 40,000 (due to alignment issues with the truck, no fault of the tire). Trouble free daily driven miles (rain, snow, dry pavement), and lots of sandy beach time, gravel forest roads and muddy two-tracks. Truck always tracked straight, got decent mpg's, and went everywhere we needed it to go.
as far as the sidewall, yes it is soft and flexible, and that flex requires you to find your ideal tire pressure as a daily driver; but it is tough. mine had minor cuts along the sidewall and there was the one day I was moving mulch in the yard....I was parallel with a 8" diameter tree trunk that was lying in my path. I needed to have truck where the tree trunk was so I just eased the front tire up on what I thought was the trunk. Nope, it was a stubbed off branch, the sidewall was sitting on this stub, tire off the ground. I very carefully eased off of it thinking I would ruin the tire; all it wound up with was a little tear in the rubber that let the white show through.....