The high voltage contactors would have to be inside the ESS to allow disconnecting the ESS terminals for safe transport, vehicle assembly, and servicing. I think there is a basic ESS schematic posted elsewhere on this site that showers the contactors.
The cables from the ESS to PEM could be replaced with a three-way cable (probably $1000 from a good outfit such as MTG Moltec). This cable would be connected to a separate box with contactors for the ChadeMo connector. This box with contactors will be required to keep high voltage disconnected from the ChadeMo connector except when charging. Contactors can be purchased from Panasonic, GigaVac, KiloVac, or others. The box will also need a microprocessor with mutiple CAN transceivers to communicate with the ChadeMo charger and one or more vehicle CAN networks. Count on at least another $1000 for the box.
The box will need software. A roadster and a ChadeMo charger will be required for development and testing. This will not be free. Changes to the Roadster's firmware may also be required. That could be REALLY expensive if reverse engineering if required.
This project sounds like a worthwhile follow on to the J1772 conversion project and the OVMS project.
GSP