Planes also have a very high safety bar to begin with, which cars do not.
Same thing about trains, there's very little value in doing so, and resistance in the form of unions in some locations. Some trains are fully automated though, here's an article with some more info: https://motherboard.vice.com/en_us/article/wnj75z/why-dont-w...
Frankly having some dude from Toyota, who don't seem to be very invested in this space, tell me he doesn't think it's going to work isn't very convincing. Chris Urmson saying it might take up to 30 years is far more convincing: http://spectrum.ieee.org/cars-that-think/transportation/self...
But that's 30 years for the entire planet, not until it works at all. WayMo is already letting people ride their cars in Phoenix - presumably one of the places with good weather and easy roads, so I think metro-level deployment in the next 4 years seems about right.
[EDIT]: And on the topic of trains. The MTA in NYC can't even seem to handle basic technical projects, like upgrading signaling infrastructure, or just extending a rail line a few miles without spending billions of dollars, so there's probably a decent chance that some of these are not automated due to sheer incompetence.