Ryan,
Nice fabrication job. Looks neat and tidy! Good job.
As Chris mentioned, there might be an issue with air trapped in the driver side cooler. You could drill and tap the upper tank of the cooler and install a bleeder screw. This way, you're assured of a completely filled oil cooler. However, at a max. of 200ºF, you might want to quit when you're ahead.
Regards,
Sherwood Lee
http://members.rennlist.org/911pcars