Upgrading FreeBSD

I decided it was finally time to take care of our old FreeBSD server and get it running something supported. This box is the main server for our household. It processes mail, provides network services (imap, dhcp, dns), houses photos, music, video, and acts as a web server for the house, including a calendar and addressbook. So it's a rather important box for our family and when it is down it is missed. In fact, during this latest upgrade my wife asked me at least 6 different times either "can I get to my e-mail yet?" or "can I get to the addressbook yet?"