It would be an interesting approach. Of the things I listed (software, backend server, API, front-end), they could use the same backend server, API and front-end for the Model S. They would only need in-the-car software. They could even use the Roadster as a test-bed for the system to be released on the Model S to get plenty of experience and the bugs worked out.
They do have a great record of supporting their roadster owners (gifts, events, priority ordering, etc), but I just can't see them investing the time into releasing such an extensive new feature for the roadster, though (particularly as it wouldn't be available for the pre-2.x cars without the prerequisite hardware).