So, I followed the Postfix/Dovecot install guide for Debian 6 and internally everything is looking good. Ports are reachable externally but Authentication always fails.

When I select POP3 in outlook 07:
Without Secure authentication: rejected plaintext
With: rejected login with secure authentication

When I select IMAP:
Always get general authentication failure regarding no supported authentication methods supported by the server.

in mail.info Imap attempts say:
Disconnected no auth attempt
pop3 say:
aborted no auth attempt

Any ideas on how to proceed from here? I've done a bit of searching around without really finding anything useful.

So, As an update I've actually fixed this but I'm still having some small problems.

1. even though the setup for Debian 6 should have required authentication for smtp I think, it really doesn't. I can telnet to port 25 on my linode and send messages with no authentication. The starttls line shows up as it says to check for in the guide.

2. Outlook setup succeeds but for some reason I never actually get my new mails in outlook though I can check them with mailx from the terminal on my user.

Any ideas on where to go from here? I'm completely new to email services and so this is quite an experience.

Don't know which guide you're referring to, but here are a couple of ideas:
1. When you're testing if you're an open relay via telnet, make sure you connect from a remote host. Often the rules are looser for connections from the local host.
2. Don't confuse what Microsoft calls "secure password authentication" (NTLM authentication) with password authentication over SSL/TLS.