You say there's no possible way, no matter how carefully a city-TLD is developed, that it will assist the residents and organization of a city. That there are no lessons to be learned from. That all hope is lost.
I think there are plenty of things one can do to improve the life of a city, but squandering hundreds of thousands of dollars on a vaniity TLD is not one of them.
That's why I'm hear asking for lessons from positive experiences. Are you saying you can't find a single one. None?
There's .CAT, which has a rather unique set of historic, political, and geographic circumstances that is unlikely to be repeated anywhere else. Even there, it's at best a modest alternative to .es, and has seen considerably less use than .CH or .HK, each of which covers a population similar to Catalonia's.
This is the wrong place to look for naifs who are foolish enough to imagine that that new TLDs are anything other than a speculative money grab.
Are you absolutely certain you're not throwing the baby out with the bath water?
If there were a baby in with the bilge, we'd have seen or more likely smelled it by now. By the way, is anyone here other than me the registry for an actual existing municipal or county domain? R's, John