Monitor is not recognized via a KVM switch
The issue appears to be an incompatibility in the DVI Cable types. I was using a DVI-D dual link cable and swapped it out for a DVI-D Single link one. My monitor is connected to the KVM also with a DVI-D single link. 

I presume somehow the MacBook was detecting dual link support, though the KVM does not support it I believe. By switching the cable I guess I forced the entire chain to be recognized as single link only.