Demopolis, AL, United States

With a population of just 7,162, Demopolis may seem like a sleepy river town, but the reality is far from idyllic. The bureaucratic headaches are persistent, from the city's messy 19th century land disputes to the ongoing political squabbles over the county seat. And the sultry, subtropical climate is a mixed bag - great for cotton farming, but also breeding grounds for yellow fever epidemics. Still, the city's historic riverfront and antebellum mansions have a certain rustic charm, making Demopolis a potential draw for those seeking a slower pace of life. But for most, the tradeoffs simply aren't worth it.