Who is the service provider? What kind of account do you have?
With most providers, it's not possible for the OBi to send differing caller IDs with the same credentials; with some, the OBi won't be able to distinguish calls based on destination number, either. However, if you are paying separately for each DID and for outbound calling, it should be a simple matter to put the numbers on separate accounts, which the OBi202 can easily handle.