A little history. When I took the truck in for it's first service under the 2 year free maintenance, which includes tire rotation, the service manager told me they never rotate dually tires. I should have questioned it but didn't. At about 15K I took it to a local shop for an alignment and they said I should do a rotation by dismounting the tires since the front and rear wheels are different. There was no abnormal wear at that time. I did that and everything seemed fine for a couple of 1600 mile trips. We drove it about 125 miles yesterday and it still drives normal.
I took it back to the original place that did the rotation and they said I need to rotate and balance again but had no reason for the cupping. I took it to the dealer and a different guy said I need to rotate and that the abnormal wear could be from the heavy load. Go to another tire shop and they said I need to do a complete dismount rotation and balance every 3K miles since it is a dually ($$$$). They thought the cupping happened because that tire was on the front for too long. I left.
A friend of mine who owned a tire shop for many years thinks it could be balance but I feel nothing in the steering wheel. I'm thinking something mechanical but it is hard to say. I do have a set of Air Lift bags on the rear but that should not matter. I keep them at 5 pounds when empty and only run 25 when pulling the Winslow. I'm due for the last of free maintenance from the dealer. I will have them check the shocks, do a rotation and balance and then just watch them. Not sure what else I can do.