Bainbridge Island, WA, United States

The population of 24,825 may seem idyllic, but Bainbridge Island's bureaucracy is a persistent headache. As a suburb of Seattle, it offers a 35-minute ferry commute, but the island's irregular coastline and hilly terrain come with their own logistical challenges. Despite the affluence - the median household income tops $88,000 - the city government must coordinate an emergency flotilla of civilian vessels in case of road and ferry disruptions. This island paradise is best suited for those who can navigate its administrative complexities.