"We need Cummins to comment, but the only reason I can imagine for why the transmission would downshift by letting up on the accelerator on the uphill run is because the truck would have lost some of its speed... "
I agree.
I have tried all different ways of towing. The trans/engine know what gear to be in when climbing a serious grade. On a big grade I just hold it to the floor and it will downshift when needed. I have manually dropped a gear and it made no difference or lost speed so I let it upshift. My 11 HO with 68RFE was different it seemed to pull better in the higher rpm's. This 15 with Aisin pulls strong at 2100-2300. Temps with this truck are never an issue even when pulling 14 percent with 33K combined. The trans and engine run cooler than the 11 did.