It is not so much the specifics of the BART strike described in the article that I find relevant, as it is the general attitude displayed by the “lucky elite class of tech workers”. [1] There is certain mix of privilege, arrogance and ignorance reflected in the idea that all it would take to implement Obamacare is to give 20 start-ups $15M each, and the problem would be solved. Voila, a quick, easy and financially viable technical solution! Sadly, the problems runs much deeper than just the technology (see other comments reflecting on procedural and political issues hampering development, changing requirements, unrealistic expectations and so on), and to ignore the systematic issues is naive.
I get where you're coming from, but it's not just the privilege issue. Fundamentally youth often has the ignorance to see the path to success where the more experienced can only see the roadblocks. Usually (especially in government) they'll quickly get clobbered by reality, but every once in a while they'll do something all the graybeards thought was impossible.
That's not to say hand-wavy armchair criticism of what is obviously a quagmire isn't annoying...
Jacobin is such an annoying magazine. Every time I commit to seriously reading (as opposed to skimming) one of their articles, I still come away with the same conclusion: that it contains almost no substance. Though I guess it's a pleasure to read the flowery language if you already agree with the premise.