Stoll was one of the first to hop on the Internet bandwagon, and he thought he could get lucky twice by hopping off the fad before it became passe.
As for the crazy from the other side, read anything by Nicholas Negroponte at the same time.
A lot of young people, especially young hackers, think like authors of science fiction novels, where there is some grand society that they have designed, and how everything is happy. Why don't people get on board?
First, they don't trust you to be right about all the trade-offs. This mistrust only increases when you tell them to get with the times; it's clear distaste for their preferences, so it only signals that you don't value their input.
Second, even if your new society model is better, you have to get people to use it. And if the way you transition is "everyone give up your old thing, then we will all move to the new thing, trust me," they will do the opposite of trust you.
Self-driving cars are a very nice transition, because no one is forcing them into use. You can have one if you want. You can hear your friend talking about how useful they are. You can try it out, and if you don't like it you don't have to use it.
"No one owns a car" is not a nice transition, no matter how awesome you think it is in the latest novel you read about able-bodied and pretty 20-somethings. Public transportation really sucks in a lot of places precisely because making public transportation awesome gets less priority than a bunch of other things, like demanding that people get to bring their pets or bikes on board, or the homeless people using it as a place to sleep.
You can make a very good case that social justice requires letting the homeless sleep on the buses. That's fine. It may even be the right call. But it means that no one else will want to use the buses. (NYC has cops every block to keep the homeless moving along, and their public transport is pretty nice.)
Buses could be awesome, if they were managed like Google buses. I would love to take one of those to work. But look at all the grief they get from the left. Grand ideas for re-imagining society will face opposition from places you would never have imagined.