Another day and OS X comes to the rescue again. This morning we had a network outage. When it came back the proxy server wasn't alive and well. After logging in to the iMac, using Fink to install Squid and WebMin to set it up we had connectivity back for the office over the VPN link.
In this is the main difference between companies with a startup mentality and those with the mentality of huge corporations. Huge corporations (and those wishing to be huge) get so wrapped up in how it's "supposed" to happen. It's all about process and ISO. ISO is not a bad thing, but in many companies it is viewed as a crutch to replace independent thinking. The breakdown occurs when people are scared into behaving like robots and not thinking for themselves.