Charlesbourg, Canada

With a population of 82,870, Charlesbourg is no quaint colonial outpost. The harsh winters and scurvy-prone early settlers are long gone, but administrative headaches persist. Navigating the bureaucracy to establish residency can be a persistent challenge. And while the fort's strategic location once offered protection, today's residents face occasional attacks from neighboring communities. This former French colony is a tough sell for all but the most resilient expats.