Well, that's a tough one to give a good answer to.
When you opt for Simultaneous Ring, "Calling Card" is the default second option (after the various extension / number choices). So, you technically can't -not- route it to the calling card.
Since the calls should originate from dialing the GV number and being forwarded, it should fall back to voicemail. I had set the ring time to 20 seconds, and maybe that was too short.
Still, the ultimate problem was that trying to use two different SIP clients (the Obi as one and ZOIPER as the other) resulted in BOTH clients disconnecting, not ringing, and no calls going through at all. Picking up a handset and making an OUTBOUND call seemed to re-connect the Obi for incoming calls again (even though outgoing and incoming use different services).