To add to this, I'm assuming "twice as large of an economy" must be hyperbole because I'm not finding any data that comes even close to that. Chicago's GDP, for example, is only ~1.3x bigger in total. In terms of GDP per capita SF is actually ~1.5x bigger (for metro areas, because that's the data I could find).

Definitely not arguing that SF doesn't have its share of management problems, but this feels like a pretty poor example.

I’m looking at just the city proper. 1.5x the GDP per capita, with 1/3 the population = half the GDP.

Then you're not looking at the city proper and we're mixing measures here. The 1.5x I mentioned is at the metro level, while your 1/3 population is city proper. That said, I'm struggling to find any kind of useful data broken down at the city level in terms of economic output, so I certainly wouldn't die on this hill.

Right, I’m assuming the relative ratio is the same for the cities as for the metro areas. Both cities have a lot of their jobs and major companies in the suburbs, so that’s probably not an unreasonable assumption.

Chicago’s problem is that it’s in a state that until quite recently taxed like a red state (3% flat income tax!). But that’s on the revenue side—it has nothing to do with how much money is reasonable to spend on city services.

If taxes are the issue, nothing is stopping the one party that rules Chicago from implementing their own progressive income tax.