re: Name a city that you appreciate that others tend to look down on...

Des Moines. It gets a "boring Midwest" stereotype but it was honestly more fun than a lot of Southern cities I've been to in terms of nightlife, restaurants, and attractions. On top of that, it has a really good school system, an extremely low crime rate for a large metro area,parks, and healthcare. I would move there if I had any family connection and the winters weren't so harsh.