So I set up my Outlook for a GMail and an @live.com account. The GMail one was very finnicky, but I entered port numbers manually and got it to work as a POP account. Work halfway, that is.
Issue: Outlook got all of my old emails, and emails from a day ago, however there is a three week period without any emails...and now my new emails aren't showing up. AKA, I log onto Outlook, hit Send/Receive All, it says it works, no new messages. I log onto GMail, and look, three emails.