Andover, MA, United States

With a population of 36,569, Andover may look like a quaint New England town, but don't be fooled - the bureaucracy here is a persistent headache. While the town's 420-foot Holt Hill offers scenic views, residents face the constant challenge of navigating a divided local government, a legacy of the 1692 witch trials. And with over 200 houses once owned by the American Woolen Company, the housing situation can feel like an industrial dystopia. If you can stomach the red tape, Andover may work for the wealthy set - the town boasts over 200 millionaires, with an average income for this elite group topping $2.4 million.