You're absolutely right! It's not reasonable to compare Uber as it is today to Night School. Instead, I suggest comparing Uber of multiple years ago to Night School. Uber wasn't always huge with lots of money behind it, after all.
Uber got to the position of being the most bloated of fat VC babies by not playing nice. Night School never got that far because they insisted on playing nice. They also ran afoul of the taxi industry, who felt threatened by their business model.
We might want to give serious consideration to the possibility that one behavior pattern is not privileged above all others in all possible scenarios.
I mean if we're really committed to the Night School idea that would probably be best done as a Government program, since it's so intertwined with assets that are used heavily by the Government. But I'm also willing to bet if we gave them a couple Billion to burn, they could also make it happen. The question of whether that's worth it or not is quite different, though.