Last December I assisted somebody with setting up Mailman+Postfix. There were some confusing issues with aliases too, because /etc/mail also has an aliases file.
If you are really desperate you could add your root alias to the /etc/mail/aliases file and run newaliases on it.
When you alias the root account to a local user account on the postfix box itself, does the alias work then?
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You don't need to be a genius to debug a pf.conf firewall ruleset, you just need the guts to run tcpdump
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