IMO, it is very unusual to want to call an OBi via GV, redirect via the OBi's AA, then use GV for the outbound leg. You would get a better quality and lower latency call, by simply going through GV's AA and not involving the OBi at all. This is also more reliable and doesn't use your OBi or Internet resources.
I suppose that you might be forced to go through the OBi, if other constraints on your configuration preclude access to the GV prompt from the calling phone. However, in your situation, that doesn't seem to be the case.
From your cell phone or another phone associated with your GV account, calling your own GV number should (by default) get to to GV voicemail; just press 2 to make a call. If you need to call home, call some other number of yours, such as your wife's GV, or your landline.
If the above doesn't work for you, please provide details; there is probably a clean workaround.