I don't think this article successfully describes "why" SF is dysfunctional. I agree that the government is bureaucratic and slow, and the school system is terrible, and our government is corrupt. That's the "what." I think some of the "why"s mentioned in the article are accurate. It's true that SF residents tend to be transient and only homeowners vote in large numbers. And SF political actors see themselves through a national prism (because SF politicians tend to go on to higher office - like the Senate, Governorship, or the Vice Presidency) that encourages them to focus on relatively less important policies like banning vaping.
But I think saying no mayor hasn't been re-elected in 20 years isn't remotely unique to SF. Guiliani was re-elected, and so was Bloomberg, and so was the widely despised de Blasio. Politicians generally get re-elected everywhere. Further, it's misleading to say that Democrats always win. SF elections are often hotly contested between the dominant political factions of "moderate" and "progressive" (although those labels are always changing meaning), even if it's Democrat vs Democrat. Some candidates are law and order, and some are anti-capitalist. There is plenty of political competition in SF - which brings me to my next point.
I think it's wishful thinking to say that a "Bloomberg-type figure" would solve all these problems. The mayor doesn't have the power to solve these problems. In fact, that's one of the (many) root causes of SF's problems - in order to make progress on all the problems listed in the article, you'd need to pass ballot propositions, change most of the Board of Supervisors, elect a different school board, elect a new mayor, and change some state laws like CEQA too. The real problem is that power is too diffuse, which encourages corruption by encouraging everyone to demand concessions before any reform can be made. It also means that candidates have to run promising things they can't deliver, or things they can deliver that don't solve the city's biggest problems. That, in turn, trains the public to expect even less of their representatives.
I think another factor is that NYC's government controls much more of its metro area than SF's government does. If the Bay Area had a governmental body that covered the whole region, they'd be able to pass broader laws that, for example, funded transit across city borders. Today, most laws like that have to be passed at the state level instead, and the state is split between many metro areas so it doesn't bother to address Bay Area-specific problems.