When you look at Web Application certificates in the Administration Console (port 9443), you see what certs/key pairs are installed and can designate the active certificate. It would be beneficial to see this same information when you look at the Server Options, it would be useful to see what is currently there and be able to switch between 

In addition, if there is a cert registered for the environment that has SAN entries for each server, you should be able to designate that certificate/key pair for each server rather than having to import it for each server in the system. This should be true for both the Administration Console and the Server Options configurations.