A few notes since I first got set up:
You can configure printers directly through the CUPS web interface.
Parallel printing was throwing off lots of errors and generally unreliable. I changed the printer to a USB connection with a USB -> Parallel cable and created a new printer through CUPS. Everything works like a charm!
ssh has been locked down to use keys instead of passwords and only allows specific users a remote login. Now this has been opened up to the world at large so I can ssh into the home server.
OpenVPN is set up and running, but I am still having some networking issues and no time to fix them...
Also up and running but not yet working is saned, a scanner daemon. I can't seem to get this working with my OfficeJet 5510, I may try a standalone scanner I have sitting around instead.
I still have yet to to a disaster recovery scenario to validate the backups... perhaps this weekend. The back up server has been rock solid, except for a minor hiccup with Steph's backups...