I wanted to update this thread.
Once the trans tempt sensor was in, it was clear that overheating is an issue. The original system simply did not have enough cooling capacity (and the way the exhaust was run was contributing to the problem). Funny, that never occurred to me. I could get to 230 degrees in less than an hour of driving. The temp would hold steady for a while, but would never go down. Flat towing my Heep 40 minutes to my friends shop and it hit 230. He put two B&M coolers behind the grill with some space between them and the radiator and on the way home it stayed right at 140.
Every time I went on a multi hour drive, especially if I was towing a light load or going over Donner Pass, I was slowly cooking the transmission.
The simplest, most obvious solution - should have seen it from the very beginning.