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Given that city layout is a collective action problem, I'd argue that Arrow's Impossibility Theorem suggests that there's no coherent social rank ordering of the possible city plans. Every plan is going to violate the preferences of some individual in some way or another that feels unfair
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Something like the Tiebout Hypothesis is what I was thinking of, although I'd prefer not to use property tax revenue as the measure of success.
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I think this is more up @SimpleStacker's alley, but I don't think we know much about what people want their cities to look like, as expressed through what they're willing to voluntarily pay for.
So much of how cities are laid out is dictated by government planners, who have no direct incentive to find long-term optimal solutions. Even a city like Houston, that has no zoning, still mostly has a city-planned transportation system.
We can infer some things about which cities people like most by looking at net migration rates, but those are reactions to an enormous bundle of stuff.