I have a 2013 F350 diesel dually pulling a 36 ft fiver. I will assume we are talking about non-interstate highways in states west Nebraska.
I always ALWAYS use Tow/Haul mode when I am hitched up. There is no reason not to.
Going uphill, I turn off cruise control and I don't necessarily try to maintain my normal level ground cruising speed. At best you will burn diesel at an alarming rate for absolutely no gain. Do not be in a hurry when going up or down. If the trans starts shifting down to 5th and then back up, I will generally just lock out 6th. Or 5th and 6th, etc. I usually only run about 60 mph anyway so the revs can start dropping off early in 6th and that's when I lock out 6th. I don't let the revs drop below 1500 going uphill in any gear. I don't mash the pedal in 5th just to maintain higher speed either. If revs start dropping I'll just lock out 5th and motor on in 4th. I shift down early in all gears to pick up some revs if I know it's going to get steeper. I don't use Manual mode much but might start experimenting with it. I suspect it might offer a few advantages.
Going down. I go over the crest and start down in a lower gear at slower speed. The general rule is to go down in the same gear you used coming up. I lock out the top 2-3 gears at the top. If needed, I will use the brakes to knock off 5-10 mph but you do not want to use the brakes very much. That's why it's important to start over the top at a slower speed in lower gears. Notice how the truckers do it. They don't start down going at 55 mph. I would never use cruise control going down and ALWAYS make sure that Tow/Haul is on.
** I drove it this way going both up and DOWN Wolf Creek Pass and did not hit the feed store in downtown Pagosa Springs.