Some of the best-known prisoners of war who held up for years against torture and despair never had the "plebe system," so why insist that it was the beatings with broom handles and pullups off of windowsills that did it? I don't recall any of the Rough Riders voluntarily going to a school because it was "harsh and cruel," but those guys were damned effective.
"Plebe" training should be hard in the ways that elite parts of Army or Marine training is hard, if they want to weed people out. But it should be professional, distant interaction...drill sergeants yelling at your face, hundreds more pushups and pullups, and running out in the cold and rain. Closer to dive school or Ranger school. Not some frat-house initiation rite or a pimply military high school refugee beating you with a sword because he thinks highly of himself and "look at all those guys dying over there so you can wake up at 5:30 and disgrace my p-way."
The closest I ever saw to Webb's training wet dream was a former Marine midshipman, pissed at being given ceremonial duty instead of getting sent to war, kick a fat kid in the balls with a steel-toed boot while he was tied up with zipties lying on the ground. Military training should be "as hard as possible" as per Heinlein et al., but hard is that last set of pullups or that crawl through the icy mud, not retarded Abu Ghraib shti. In reality, we're not going to get the benefit of humiliating torture, like my buddy being forced to piss himself in front of the female midshipmen while standing on a wall, just seven years ago. Reality is they shoot us in the head or start cutting, and who wants to waste time preparing for that...you either have it or you don't.
Practice torture? Try rowing.
Edit: That's not a dig on James Webb's military expertise, or Navy Cross-winning combat effectiveness and dedication. Merely on the system that would arise if his ideas, which are nominally sound ones, were put to work by lesser leaders. For a prime example, visit the Naval Academy.