I think we have quite some experience with insuring unsupervised systems. After all, I am not supposed to supervise my coffee machine, but if it causes a fire then my insurance has to pay.
On the other hand, I think that the politics of self driving cars could get rather interesting, especially if widespread adoption is fast, say 5 years until a self driving car is no longer extraordinary and 10 years until one just assumes that a new car is self driving. Then I think we get a initial phase, were they are seen as modern. After this, when every single accident gets widely reported, I think it is possible that the public completely splits, on one hand the traditionalists, who maintain that only a human should drive. And on the other hand the people who say that self driving cars are safer than humans. And the laws will shift according to the relative strength of the two groups. ( With probably some rather ridiculous political compromises in between, perhaps you are allowed to read a newspaper, but not to drink coffee. )