Shoot, no history. I'm running out of ideas here -- below are just guesses. It's especially puzzling, because AFAIK no one else has reported this problem.
Possibly, something goes wrong with the protocol, such that GV doesn't see the call as properly answered, and it continues to try other destinations. If this is the case, I would expect the trouble (if it occurs) to always happen within the first minute of a call.
Possibly, you have a talk-off issue that is inadvertently triggering some new, unpublicized feature of GV. I confirmed that on an incoming GV call, DTMF events do get logged to syslog. You could set System Management -> Device Admin -> Syslog -> Server to the private IP address of your PC, run Wireshark or a syslog server to capture traffic, wait for a failing call, and see whether any false keypresses were detected. Also, something else might be reported that proves to be relevant.
It may be possible to work around the problem, without understanding the cause. For example, have GV ring to a free Callcentric number, rather than Google Chat. Unfortunately, you are already using SP2 for another GV account. If you use the second account with the OBi only for receiving calls, you could funnel that into the same Callcentric number, which would free up the SP2 slot.
If you haven't already done so, you might try shutting down the OBi and answering your GV calls from Gmail for a while. It that also has the trouble, it would at least show that it's not related to the OBi; you could then pursue getting help from Google or on the GV forum.
BTW, if you want to post a screenshot that has private info, open it in an image editor (e.g Paint, if you've got nothing better) and use the Eraser tool to white out any information that you consider personal. Save the modified image and post that.