@bko its a bit tricky, so I'll try to keep it simple.
Relative to the boat, a shoreline skier DOES have to "cover more ground" in the sense that to run 38 off, they have to get maybe 65 degrees up beside the boat, (instead of ~40-45 degrees at 15 off) to get around buoy 1, THEN do the same thing but on the other side of the boat, before buoy 2. So relative to the pylon, the skier is traveling a larger Arc, and getting higher on the boat on each side (higher than a 15 off skier would), which is what the Adams have covered at length, by talking about moving the handle as high as possible on the side of the boat, as fast as possible.
BUT, if you actually traced the path of a 15 off skier from a drone, vs a 41 off skier, the 15 off skier is actually traveling a longer path. They have more rope, and ultimately are able to break the buoy line sooner, AND apex much further up course. All of this points to a longer skier path through the course, at longer rope lengths, as a general rule.