How does one achieve "privileged" status, and how exactly does the upload limit work?

Priveleged accounts: http://e621.net/help/users

The management decides who gets privileged accounts. I think only Varka can do this, and that he usually gives it to people who make a monetary donation to the site.

I'm not entirely sure about that second part. So don't quote me on that.

Post limit formula: http://e621.net/forum/show/12628

Basically, your post limit increases when your posts are approved, and decreases when they are unapproved/deleted.

That helps. Thank you.

Wait for the next batweek.

I have the ability to grant people privileged status as well, and we do not give anyone any kind of status at the moment for donating anything (because we're not currently accepting donations).

I want to stab whoever started that monetary donations get privileged accounts crap...

I was going to ask that question too, Blitz. The user help page doesn't disclose much about privileged status. It's perfectly understandable if they don't give out this status freely.