I don't have serious problem with this... but ballot stuffing and fake account registration seems the domain of SEO/blackhats or Anon. This isn't a 'cute hack' worthy of praise -- it's just abuse of MIT and Dropbox systems for no great reason other than perhaps pride.
As noted below, MIT had a significantly higher target than any other school. The jump from 15 to 25 for MIT was ~50k points while NUS (26k students) got to 25 around 25k total points. Remember that by "not cheating" there are only ~10,000 MIT students (undergrad and grad), so the goal is impossible without cheating (there aren't that many faculty members and staff).
It wouldn't surprise me if they assumed it would be cheated, so this was an attempt to improve their fraud detection. After all, it's not like these extra 50,000 accounts actually cost much to Dropbox. They each will presumably have only the starting files in them which are all duped in every other account.
I think Drew, as an MIT alum, expected MIT to script the process anyway. In fact, I'll bet he's proud that his alma-mater by-passed dropbox's flagging filters. Also, now Dropbox can look to hire new potential MIT interns and employees.
