I mean, in this case it is probably considered a net win, MIT is known for its culture of "hacks", and having to game your way into the required courses adds to the challenge!
Eh, just in the last decade MIT has seen a huge shift towards a culture of risk adversion. The administration have actively suppressed and dismantled cultural elements they do not find desireable. See what happened to Bexley house and senior house, and I'm not sure what's happening with east campus these days but some kind of construction is going on.
Still a fine university, but the days of 'hacker' culture are definitely dwindling. There are still pockets here and there, but like with old forms of communication (IRC, etc ) it becomes harder and harder to foster that culture when there are less and less spaces for it while simultaneously creating curated spaces that are so much easier to use.
