Interesting thread.
One thing I think is missing from this discussion is how significantly even the nature of transportation has changed in the era of mobile phone tech. Some context: I live in Seattle, grew up in Minneapolis, went to school in New York, and my aunt and uncle lived/live in Manhattan and have for the last 25 years. I recently got them to experiment with Uber in New York. They rarely take taxis, so it was just sort of a novelty. They hated the experience but only because they believe there has been a significant loss of "institutional knowledge" about cities (for lack of a better term, I guess). What I mean by that is this driver had no clue where to go. I think this is sort of a danger with rideshare (not that I'm arguing against it...I'm not) wherein the drivers rely overtly on the technology to guide them. Someone visiting the city can't get in a cab (uber) and say "Hey, I'm looking for x, y, and z tonight...where can I find that?" My Uncle was telling me that, as bad and dangerous as it was years ago, cab drivers were basically the resident experts of a city. They were so plugged-in to everything that they had almost a 6th sense about them. That's been my experience with Uber in Seattle. I cannot rely on the driver to get around the city at all. My experience with Lyft has been so much better that in some cases I'd rather walk the mile back to my place than catch an uber. All of this might just be the learning curve uber has built for themselves as a direct result of the rate at which they've been expanding. But it's something both companies should address. If uber/lyft really are going to dominate urban transportation (and even inter-urban transpo....uber vegas anyone?) then they need to do more than just take me from point A to point B. They actually have to know where they're going.