Hi Eric, glad the trip went well! I agree with most here, don't waste time on intake/exhaust, if you want more power then do an axle gear change from 3.73 to 4.10 (no 4.30 on GM, next stop would be 4.56 and that's too tall for what you're doing). Both axles will cost around $1500 to do at a good axle shop.
Aside from that, it sounds like you stopped the hunting by limiting the trans to 5th gear. One of the ways that the mfrs maximize fuel economy is to program the ECM to upshift at every opportunity, and it can be frustrating on rolling hills. The wind is also a factor when towing a big hard-sided trailer. As soon as the load on the motor abates a little, the trans will try to upshift if you let it, but if you need power again in 5 seconds, it will downshift to deliver.
FYI, your trans temps are right where they should be, I have never seen higher than 205 even going up a steep incline. The factory cooler on the HD trucks has been moire than sufficient in my experience, it's mainly the 1500 series trucks that benefit from more trans cooling.
Intheburbs, the caption on your pic should be "Last pic I took before the trans blew."