I've followed the Ubuntu postfix/dovecot (Maildir) setup verbatim:
https://help.ubuntu.com/community/Dovecot
What I was trying to express is that postfix is working since I can send via Gmail through my server address. However when I try to retrieve mail from my server address via Gmail no emails are found. However when I check locally on the server the emails are there. I was noting the SSL setup worked since Gmail now has strict SSL enforcement for third party addresses.
I'm new to this whole process so from what I gather I think this means my postfix is working and my dovecot is setup incorrectly. I don't want to post the whole conf, so if there's a problematic section I should post please let me know.