We're on the same page now, I did misunderstand your post earlier but Stage 2 is what I was referring to.

It seems like setting up his outlook on my computer and selecting "leave a copy of the message on the server" would work perfectly. I google'd that phrase and found instructions on how to find that option.

My knowledge of Outlook is pretty limited, but from my understanding if I check this it will download the e-mails to my hard drive while still letting him view the e-mails on his computer, correct?

You've been a HUGE help so far!!