Sorry, I had misunderstood your question; my earlier post was not useful.
If you want to call in and then place an outbound call to an arbitrary number, it may be easier for you to just call your GV number, press 2 at the main GV menu, then dial your destination number. This does not involve the OBi at all and should result in a higher quality call with less latency.
In the example you gave (New York landline number and California GV number), it could be useful to go through the OBi, e.g. if calling from a New York landline without unlimited long distance. However, if you did that a lot, just get a second GV account, with a New York number.