If this has been covered elsewhere, I apologize for bringing it up yet again:

Why cannot WN issue RR-tickets as e-tickets? Yes, I understand the award is transferable. So make it convertable to paper upon request prior to expiration . The award-holder can either send for the certs if there's enough time, or go the airport to obtain paper ones closer to the desired flight on which the other person will be travelling.
Otherwise, the awards are deducted by the kiosk electronically. Other airlines do this efficiently with electronic upgrade points.

This is not even getting into electronically transferring the award into another RR account - either from home, by mail, or at a WN counter in-person by the award-earner(saving the recipient standing in line later).

Moreover, I don't see why Companions need to see a live agent?

Mary Sunshine registers her sweetie, Georgie Porgy, as the Companion.
She purchases a ticket for herself and adds him to the same PNR.
At the kiosk, she calls up the reservation, confirms he's still going, and out pop their boarding passes.
His would be clearly marked Companion Pass, referencing her RR#. At the boarding gate, both boarding passes must be presented at the same time. The TSA has [presumably] verified that ID's have been produced matching those boarding passes.

Are these ideas that difficult to implement?