[munificent]

It's not exactly what you're getting at, but you might enjoy Christopher Alexander's essay "A City is not a Tree". It also talks about why highly planned cities can end up not working and feeling "right" in the way that older more incrementally-grown ones can.

[ttul]

Take Tokyo for example. It’s ugly and massive and sprawling but, connected with amazing transit, there is not only plenty of housing for everyone at all income levels, but the place is also just totally rad.

[astrange]

Tokyo is ugly because of its tropical summers; if you tried to build the Western idea of "not ugly" there would be mold and insects everywhere.

[smallmancontrov]

It would be more convincing to rage against planning if the backdrop wasn't a situation clearly created by the complete absence of planning. Obviously there's a middle ground. This isn't it.