Former Chicago suburbs native. Once you have kids, you’re not willing to take them to the Bean on a weekend and end up in the middle of a shooting. Taxes are higher in NY or SF, but if you have kids, you’re not moving there anyway (I’d pick Des Moines, IA or somewhere safe in the Rust Belt first). The weather might get better with climate change, but probably not enough to make the winters tolerable. It can get very cold, and you might as well live in Canadian latitudes those times of the year. CPS quality is low and likely to not improve in the time my kids would rely on it.

Chicago could be great, but the effort required makes it a deep long dated out of the money call. Some deus ex machina intervention is going to be required to reduce crime, reduce the debt burden, and right size public services so a productive tax base will stay. Ideally, one works remotely for a Chicago firm and visits when the weather is good (between Memorial and Labor Day).