In general, I don’t consider myself too much of a sysadmin dummy, but it seems that getting my mail set up was much more complex than it should have been for what seems to be a fairly common set up. You’d think that this type of thing would be automated… but, you’d be wrong.

• Virtual mail – this setup guide worked perfectly (I picked this data-model over the rest I reviewed since it seemed simple and made sense). As long as you tail your mail logs to see what’s going wrong, this shouldn’t be much of an issue.
• SASL – Using libpam-mysql for SASL? Not a good idea. Here’s a much easier way, install libsasl2-modules-sql and use the auxprop set up as specified. Easy breezy. Be sure to enable TLS in Postfix’s master.cf properly and check if there aren’t MySQL connection problems (enable local TCP/IP if it can’t reach the socket)
• TLS – use stunnel to connect into/test your SMTP-AUTH

OK, once you’ve found the right guides, it doesn’t seem so hard, but damn if it didn’t take me a whole lot of searching, trial and error, and log debugging to get there.