Roaming devices might make it a bit more tricky, but some integration with OS connectivity-detection and location-awareness might help there, as well as an improved UI for actually setting it.
A really short-term bandage would be to use some less identifiable DGA, but that opens the possibility of future malware using the Chrome DGA to pretend to be legit.
Is there a technical reason why 'foo.invalid' and 'bar.invalid' (and any of the other restricted dns names) couldn't be used instead?
I suppose that the ISPs could serve those correctly to make the tests pass, but what would they gain from it except even more user irritation?
Anything I'm missing?