Isfahan (Esfahan), Iran

Capital City

With a population of just over 1.9 million, Isfahan is Iran's third-largest city - but don't let that fool you. This ancient metropolis is a bureaucratic nightmare, with locals constantly battling the city's notorious red tape. The climate is also a challenge, with searing summer heat and frigid winters. And while the city's rich history and stunning architecture are undeniable, the ever-present threat of air pollution and water scarcity are persistent headaches. Unless you're a die-hard history buff with a high tolerance for administrative hurdles, Isfahan may not be the ideal expat destination.