I've found that with 12,000lbs. the transmission seems to downshift too often at 65MPH as I climb otherwise minimal hills. I haven't tried dropping the speed to 55 MPH, but that might help. I also use cruise control most of the time, which might affect the way it shifts on hills when pulling a trailer.
You mentioned some other variables that I left out. I also use the original stock tires, and have replaced them with the exact same tire. Empty I have limited my speed to just under 70 MPH, even when the speed limit is 75 (this is, for me the hardest part of trying to maximize fuel economy). I have the same architecture as you do, but run a factory muffler and exhaust. And while I don't add two cycle oil, I do add 16oz of Power Service in the silver jug (and occasionally Howes) every other fill up, or when it drop below half a tank. I definitely see a correlation between using it and fuel economy. A while back I read something here about the possibility of enriching the fuel with sulfur with cutting oil, which has a high sulfur content. Never tried it, but since you are adding oil to your fuel, you might consider it.
Towing slower will make it worse, you would have less H/P and volumetric efficiently at a lower RPM. The trans will downshift to compensate, thus can wear it out if the trans is consistently down and up shifting. One thing to do is anticipate the grade, turn off overdrive, this will bring up RPM to help pull the load.
I have a 6-speed stick, so when I have that 11K in tow going up a steep grade I will downshift to 5th and maintain 55mph.
To show you what torque and H/P can do, my nephew has the new 6. 7 Ram with the 6 speed automatic trans. He pulled my trailer with his truck, on the same grade, it was a night and day difference. 11K is no sweat for that powerhouse. The trans did make one downshift to 5th OD, and still pulled the grade at 70 mph. But this comes at a cost with MPG, more boost, more power, pulls heavier loads at a faster speed.
The question one needs to ask, how much weight in tow and how fast up a grade do you want to go ?
Our trucks work good with 10K to 12K, but if your going to pull 14K to 16K you need the 6. 7 Cummins. Otherwise I would need to be in 4th gear and you in 3rd gear auto chugging up a grade.
Removing the muffler helped the MPG by 1, installing the TAG helped MPG by 1, adding the two stroke oil helped MPG by . 6
Refinery switchover from diesel to ULSD, removing the sulfur from diesel, but that also gave us a negative of less cetane, which reduces the BTU's of the fuel. Less torque and MPG of the new fuel. My own calculations was -2 MPG loss for the new fuel. All of my hard earned MPG achievements were taken away. The only other thing I could do was drive slower, from 70 down to 65, and I got back that 2 MPG. Just imagine driving slow with the old school diesel, I think I could get 26 MPG?
As far as adding thread cutting oil, I don't think it is that simple. By adding sulfur will that bring back a higher cetane level?
I use the two stroke oil to help with lubricity of the injectors, two fuel pumps, top cylinder life. And the side benefit was a . 6 mpg increase.