Like any other high speed train concept, this kind of thing *might possibly* work in high density, small geography Japan, Western Europe, and a few places like SOCAL, NORCAL, and NY/DC corridor.
But there are many problems...
Infrastructure: Imminent domain for the rail would be the biggie. You could use existing railroad rights-of-way where the rail is straight enough and in unpopulated areas. But existing rail with tight curves would not work, and NIMBY's would oppose any significant expansion of status quo use of existing rail lines on grounds of noise, safety, and visual clutter.
Weather:
1) It would be under ALL weather.
2) It cannot deviate to avoid weather.
3) It cannot climb to avoid weather.
4) It's still an airplane (and fragile looking), and would be destroyed if it flew through a TS or severe ice.
Security: The plane is easily accessible by bad guys along any point in it's route. The power supply is easily accessible by bad guys along any point in it's route. A crash would make big headlines.
I think the most likely mass transit revolution (other than improved airliners with lower cost and environmental impact) will be high-speed underground tubes. That solves most of the security, imminent domain, and public perception issue. But it will cost huge $$$ to drill underground tunnels over vast distances (ex. Chunnel).
These visionaries (including Uber) are going to learn the hard way that the urban public will probably not be very keen on a massive increase in low-altitude airborne noise and clutter.