250 fahrenheit at the pan is quite hot for a 4R70W transmission. I do not recall the exact set-point of the thermal bypass valve for the transmission, but for this vintage you should be running at 190F or less under normal operation. What is the build configuration of your truck, does it have max trailer tow with an oil to air aux cooler on the transmission?
It would be interesting to monitor sump temperature when you are towing. It also maybe worthwhile to scan for codes, I believe the P0218 code will store if it is set.