You've just dodged half the questions, though. Failure of user's own equipment will be a nightmare, doubly so as it's virtually impossible to tell the difference between a genuine problem and someone who is just claiming the PC ate the file. Working at a university, we can manage a lot of this because we provide 24 hour access to tightly locked down systems that we know will work (or, if they don't, we'll know because we get a hundred support queries instead of just one).
I'll accept, we've never had a serious problem with staff-provided PDFs. For coursework submission though:
1. During first rollout, we had a significant number of students who saved their file to the desktop, opened the web application and clicked the "Upload" button. Apparently the step where they needed to tell the system what file to upload was a surprise. We now have to e-mail out cryptographically signed receipts when a file is uploaded, to confirm the system has the file.
2. Students rapidly figured out however that they could upload work, get a receipt, then delete it (as if to replace it with a new file) and claim the system had eaten it. So now we're also tracking all work submitted over time. Marks and feedback are also attached to the file uploaded (not the assignment due), so that if a student is allowed to re-submit after the due date, any marks entered are correctly preserved.
3. Students submit work to the wrong places, so now we have time locks (maximum number of weeks before work is due, that they can submit), and the ability to readily move work between assignments.
4. Students submit the wrong format, either because it's what they have, or because they haven't the faintest clue what they're doing. You would not believe how many people think they can convert .doc to .docx or .pdf by renaming the file.
5. Students submit files with distinct oddities. PDFs with security turned on and printing disabled for example. Word documents that open in some versions of Office and not others. Are these okay? Can they be filtered out?
6. Viruses; both Word and PDF documents can carry viruses, so now you have to virus scan incoming work. Can you reject work if it matches a virus signature, or do you have to keep a copy of it quarantined until a techy can examine it? If you reject work but the student's done it, is it late?
Also, are you suggesting that coursework doesn't need printing, or that the school prints it themselves? The former doesn't match the feedback we've received from academics (or; you try marking 30 essays on computer and tell me how you feel about the experience), the latter is an extra cost to the school.
Long story short, electronic coursework submission is a lot harder than it looks. Support is getting there, but this is really waiting on there being proper generic frameworks for supporting it.