CPS is uniquely dysfunctional with the number of times they strike. I had three kids in Coonley and the mood was constantly adversarial. The teachers see everyone as the enemy. It was pervasive and nasty and it spilled into the classroom. Like many other things it's become self-sorting. The good teachers mostly want to take a pay cut to go to a private school where the culture is different, and same for families that place a high value on education. The public system is the residual, and I'd say this is proven in various grim stats.
I really just think the culture is ugly, I don't know how else to say it. Everything felt negative, everyone was angry. Leaders (and the majority who elect them) de facto support and enable all this dysfunction because for various reasons it's now part of their ethos. It wasn't until we moved that I understood it, and I admit it's very difficult to articulate. I'm not saying Chicago is a hell hole, but the future of Chicago is at best stagnant to me...real estate values partly prove that. Migration stats, especially among high earners, should be deeply concerning to anyone involved. I haven't even touched on how financially screwed Illinois is.
The city just looks checkmated to me. This isn't Rochester but it's clearly in decline. When the companies start leaving is when people should start taking it really seriously, and we just had Caterpillar, Boeing, and now Citadel all bail, Citadel quite publicly. We can debate all sorts of things but the scoreboard here, the ultimate things which we'd use to measure a city's overall health and direction, is deeply and objectively troubling.