This is not a very radical idea. It is known that people are averse to losing things they already have (even in exchange for equal or greater benefit). I'm glad it worked out for Lyft without too many ruffled feathers, at least according to the comic. I'm glad this sort of idea continues to get media exposure. It needs it.
An example, it is absurd to me (and most urbanist types) that Manhattan still has free street parking and that all the East River bridges are free. Congestion pricing in Lower Manhattan was on the table during the Bloomberg era, but never made it through. It should have.
Congestion pricing proposals for publicly-owned infrastructure always run into the same problem: taxpayers paid for the building of the infrastructure, they already own it. Charging what the market will bear effectively turns the infrastructure over to the relatively wealthy to use. Making people watch as the rich get exclusive use of the infrastructure every taxpayer paid for never goes over well.
But what if charging what the market will bear means the rich are paying for the cost of the thing and then some?
Anyway, my impression is that opposition to things like congestion fees come more from affluent commuting suburbanites than the poor (who probably already rely on transit anyway).
No, because the point is that cars specifically are Pretty Bad for cities (noise, air quality, inefficient use of space, dangerous) and should be discouraged (and economic incentives work). Mass transit is generally far less bad and should be encouraged by economic means.
NYC sort-of does this by not using zone fares, so long trips from far-away areas (read: poor parts of the city) cost as much as a brief trip through a rich area.
Because of geometry: cars do not scale well in cities. Only so much land to go around, you want (need, really) people to use more space-efficient modes. Supporting cars is particularly expensive compared to other modes because of how much space cars take to move around and park.
An example, it is absurd to me (and most urbanist types) that Manhattan still has free street parking and that all the East River bridges are free. Congestion pricing in Lower Manhattan was on the table during the Bloomberg era, but never made it through. It should have.