@Brow98n In what scenario am I attempting to set 2 default routes? I am thinking an assumption was made here, probably due to my bad explanation of the problem.
When I log in twice with the same user it is from different machines as I would not be able to easily determine which tunnel was broken. I do not have OpenVPN overwrite the default route on the client, I just advertise routes to specific endpoints inside my networks. I do not believe that OpenVPN easily supports a per user route advertisement, AFAIK, it is a function of the OpenVPN instance. In the end, if I can give routes to device list A to user list A and device list B to user list B, that would accomplish my goal of 2 instances, and work around my issues I have on the second instance.