Re: Trailering and overdrive
I would not use OD on that transmission, mostly to eliminate the added load on both the smallest set of clutches in that transmission as well as the added torque converter heat. Chances are that on a heavier trailer, you may even get better fuel economy in the lower range. That is definitely the case on my smaller Ford Ranger when towing, especially around town and at lower speeds.
The 4R70/75 E and W transmissions are a pretty well proven design with roots going back to the late 70's. The weak like when towing is the converter on these. A serious trans cooler is in order for any towing but that should be a given on any truck these days. It's a very capable trans with normal use and maintenance. The later 4R75 transmissions have a better shift program but differ little from the older model.
Although I'd generally say not to two in OD, I pretty much judge by how the load feels behind the truck and the terrain at hand. I would pretty much say that if you can feel the truck working to tow the load, turn off the OD. If you were pulling a light boat in which the truck doesn't even feel, then OD would not be a problem. I would never use OD on hills.