Chaohu, China

With a population of 727,162, Chaohu may seem like a sizable city, but the reality on the ground is a persistent bureaucratic headache. Formerly a prefecture-level city, Chaohu was controversially split and absorbed into the neighboring city of Hefei in 2011, leaving a tangled web of local governance that can be a real hassle for residents. And while the city boasts a picturesque location on the shores of Lake Chao, the weather is far from ideal, with a climate that can be unforgiving. Overall, Chaohu is a city best suited for those who can navigate its administrative complexities and don't mind a challenge.