It's been so long (two weeks) this thread is probably dead, but I wanted to post how this wound up. After meeting with the poco planner and also the AHJ, there will be the two meters, grouped on the existing residence. The overhead service will stay but be upgraded with larger wire. I'll probably bring it to a gutter and then to the existing service which has a meter and also from the gutter to a new meter/main which will serve as the disconnect and then underground to the new residence service panel.
My main concern in all of this has always been how to feed the new residence Since it had a service panel, I knew if I ran a grounding conductor with the feeder I would have a problem per 250.32 (B) ('08) because of the bond between the grounded conductor and the grounding conductor (not modifiable). In my meeting with the AHJ I argued for the exception in that paragraph, because there was no metallic connections between the buildings, and we could easily comply with the other conditions as well. The exception is directed at existing buildings, and that's not really the case here, but given the situation, the AHJ was willing to consider it. That exception would allow a three conductor feeder with no grounding conductor from the new meter/main disconnect with the grounded conductor connected to the new service panel and uffer in the usual manner. That may be what Augie47 had in mind. And so that's what we'll be doing.