Cityimrov, I think you're coming at this from a perspective that is opposite of a Bostonian or resident of similarly large/dense/expensive city. Valid questions, but I don't think you grasp how different it is with regards to getting around in these larger cities.
There will never be an anti-transit push (quite the opposite). Everyone knows transit's shortfalls, delays, etc. Employers are forgiving, an occasional "delay on the tracks" excuse is no different from an occasional "elevator was down" excuse. It's too difficult and expensive to own or use a car...even rich people take cabs/town cars/transit to work because few have the ability to even have parking, let alone pay for it, let alone the patience to sit in a funnel of 500,000 people into 2 square miles before you even begin scouting for your spot.
It's one of those "everyone's in it together" moments/truisms of the urban cities that are just not felt or comprehended by folks who have never had the pleasure of living in an urban environment. Progressives in Jax are pushing for transit even though it's super cheap, easy and convenient to get around by car and transit is not needed. In Boston, let me tell you, transit is NEEDED. When it shuts down, it's an inconvenience that everyone faces together. It's no different from being snowed in...smart people who are totally dependent on every hourly wage they can muster simply plan for a rainy day.