Pskov, Russia

With a population of 574,480, Pskov is a remote, provincial Russian outpost that offers little to lure expatriates. The harsh climate and heavy bureaucratic burdens are persistent headaches, while the region's tumultuous history and border security zones add an aura of isolation. Though Pskov boasts well-preserved medieval architecture, this cultural draw is unlikely to outweigh the practical challenges of daily life. Overall, this city is best suited for die-hard Russophiles willing to brave its considerable inconveniences.