I appreciate the reply and I think you pretty well summed up right where i am. I'm running 2 OSX Servers in separate geographical locations with a VPN connecting them. The VPN is slow enough that I would need the image on each server and set each as a netboot. I've built a custom image before and deployed via netinstall - which worked fairly well. The primary issue is each person has custom settings, programs on each computer that are not a big deal for me to restore, but I would spend a good while restoring/helping folks get things "back to normal" if I deployed an image.
With that, in the past, I have also just copied the image to each workstation with ARD copy and then used ARD to issue a command to login and kickoff the installer as admin. I could then use ARD to bounce around to each machine and click "next" and do the one time login where the machine asks the basic post upgrade questions. I just figured there was a shell script that would copy the upgrade file, kickoff the install and do it silently in the background. No such luck?