This is an interesting thread but I think the question is overly broad and it would be more helpful to break it down. I would propose the following questions, and in some cases I have a strong opinion:

1. Does Detroit have the worst crime problem among mid size cities? I think not. It's bad, but not the worst.

2. Is metro Detroit the most dysfunctional region in America? Absolutely yes. Thank our state constitution with its ridiculous "home rule", and the racial politics of the last forty years.

3. Does Detroit have the worst schools? Not at all. Some good, some frightful, on a par with other big cities.

4. Does Detroit have the worst neighborhoods? Not at all; but Detroit perhaps has more of its overall land mass swallowed by blight and abandonment than any other mid major city.

5. Does Detroit have the worst transportation? Both for the city and the region, yes; and there's not even a close second. Our roads are crumbling and our transit would be embarrassing to a third-world mayor.

There are parts of civic life where Detroit isn't bad at all, city or region: libraries, parks, museums, access to good live music, etc. But I think if we want to improve things, it is helpful to focus on our biggest problems a la Pareto, rather than just gripe about how bad we are overall. We're not bad overall; we're bad at certain critical things.