On a hunch and because this system is so ridiculously fast (It's one of those custom gamer boxes ), I added a 5 second sleep to the script. This fixed the issue. I was able to cut it to 3 seconds later on.
The reason for this is actually pretty simple. The system is so fast that it is fully operational with the Unity greeter fully displayed long before the network interface comes online. No network, no synergy and no ssh.