Jesus, I'm not looking to be able to do everything, as you seem to think. The specific things I'm looking for I don't see why they're so grandiose. They don't seem more elaborate or fancy or valuable than the things that ARE given for free, but just better in some ways. For example, NOT synchronizing would actually simplify the process. I don't even care about a fancy interface or anything. Something totally utilitarian is fine, even if it's covered in advertisements. I really don't care; I'm a pragmatist.

Go back to being a character in Infinite Jest.

I don't drink, do drugs, or play tennis. :P

If I can suggest my 2 cents, you can try to use several Google Drive accounts. Each one offers you 15 Gb, so it might be a solution...

He's already said he doesn't trust Google. I can't blame him for that. :)

There's not a problem with privacy in Canada, is there? Because so far I've ruled out everything else on the list, and the only one remaining is Sync, which is in Canada.

Edit: EVERYTHING else is either from one of the countries you mentioned, or it's something like Google or Apple or somebody who doesn't respect privacy AT ALL, or it has no free version or only a limited time trial, so Sync seems to be the ONLY one that remains.

I'm not sure about Canada, never heard anything about it. But I'm no expert or search for this kind of info specifically. What I said before is just things that I heard or read randomly on the net.

Not implying anything, but if it's something illegal, probably any company in western countries will comply with law agencies requests.

Alright, thanks.

How about Microsoft's Onedrive? You can share files with specific accounts. Or was that already mentioned?

Microsoft, now there's someone I want to trust with my data... nope. Good try though; I know you mean well. I think I might just go with Sync, but I'll look into it some more tomorrow.

* Edit: disregard this *

I think, what you are looking for is a platform for teachers. I searched a bit, and found this:
https://www.pbworks.com/index.html

You will need to hit Get started and pick Edu Hub. Allows you to set a doimain name, manage user accounts and share files. See if this serves as a good example to what you are after.

Yeah, I figured as much... but thought I'd just mention it.

Oh great, so Canada's out too. I guess NONE of them are any good. What's this, under_the_hood? It looks like some kind of a chat room and presentation software like PowerPoint or something. Are you sure it could do what I need? How does it work?

EDIT: Oh I just noticed that it does say "wiki hosting and file sharing". Is this something where multiple different people with different accounts could all upload and download files to share back and forth with each other? Or at least, would it allow multiple people to log in simultaneously with the same account and not conflict with each other?