Is the point here that you want to make your bike easier to ride, more efficient?
There are two issues there, one is the ascent, and the other is the descent. BOB can jacknife you on the way down, which would suck.
Going up is mostly a fitness mater. People drag the trailers in all kinds of terrible terrain. I think that paniers and racks are lighter and ride better than a trailer, but that also depends on how light your paniers and racks are and how much you put in them. There are some heavy panniers and some very heavy racks. Not dragging the extra wheel helps too. If you live on the BRP, you could certainly run a sequential test.
It probably doesn't take a lot of training to get yourself past the differential hump. You know, if you worked up to climbing some huge hill, it took you 5 tries to make it. Then you summit with panniers, how many further tries would it take with the BOB?