Where I study, IT staff try to be use- and helpful, and not just to keep their jobs.
And I'm still a few months away from college. It looks like Stanford has some pretty good systems overall, but just as a datapoint, the design of Axess (the system that appears to handle pretty much everything--course signup, financial aid, etc) is much uglier (and a little harder to use) than any commercial site I use. It gets the job done, it probably dates back to when all sites looked like that, and the people in charge of it don't have enough incentive to give it a facelift.
I can’t complain but it’s probably also true that something like powerful tools for seamless online collaboration is outside the scope of university IT departments.
(The university actually uses moodle which would offer some useful functionality but not even the lecturers like it. Asked whether we should use moodle to upload our stuff: disgusted-look “Uhm, it would be nice if we could use Dropbox, that’s a pretty cool service. Do you know it?” :)
Dropbox is providing the service to 5M people, and the whole business is built on it being spectacular. The economies of scale mean that they can afford to make tiny improvements, and they have serious incentives to make it as great as possible; otherwise, they go out of business. (In fact, otherwise, they would have gone out of business long before they made it to 5M users.)
Good OSS can fix this to an extent--if someone started a really good host-your-own Dropbox project, every university could use it, getting you similar scale when it comes to coding it, so people would contribute from all over to make it great, and the IT at each individual university would just have to deploy it and update it as it improves.