We have a 40' motorhome with a 20k towing limit, 360hp Cummins L9 with 1150 lb-ft. Our toad weighs about 4600lbs (2-door JK Wrangler with steel bumpers, winch, etc). Gross combined for the motorhome is rated 60,000 lbs and the rig wet and loaded by itself is north of 35,000. I didn't get a weight this last weekend but my napkin math says just below 40k combined with the Jeep behind it.
We drove from Seattle to Newport, OR, down I-5 and then crossed over to the coast on Highway 20 at Corvallis. 20 goes over a minor mountain pass but there are a few sections with some good grades, maybe 5%. The L9 was happy to pull the steepest of those at 45 or so, which, honestly, a little more lethargic than I was expecting, but it's barely broken in. 1800-1900 RPM seems to be the sweet spot and once it gets into a gear where it can run that consistently, I feel like it could pull much more at that speed. Total trip was about 625 miles, averaging around 7mpg.
Now, I've towed a lot with a smaller diesel. Had an '06 Jayco Seneca 34ss, which was about 36', had a 300hp 550 lb-ft Duramax V8 and 5-speed automatic. We pulled a 7k trailer with that from Seattle to Minneapolis a couple of times and it did very, very well considering. 35-45mph on the steepest of passes including the Rockies, but that was everything it had at 2800rpm. It was fully loaded to its 26k gross combined limit and maybe then some. Fuel mileage was much better, 8-9 while towing and as good as 11mpg when not towing when keeping speeds around 65.
Look into a TSD Open Roads card if you get diesel. We saved $70 across two fill-ups this last weekend alone.