Stage 1 is the way to go. I checked out "Rules and Alerts" and saw I could make a custom rule that would automatically forward any messages he receives to be sent to me. I can set this rule only for messages with the appropriate subject line so I won't get any of his other mail either. This sounds like it should work, I'll just have to have him send all of the original e-mails.

*EDIT* Is there a way that I can send mail from his outlook though? Besides taking his computer and sending out e-mails, what would be the next best way to do this (is there some type of special Delegate option maybe)?

I'm not sure what email server we're using (SMTP if that makes sense). And yes, there is an admin managing the server but the turnaround on contacting him would be pretty long.