Feltre, Italy

With a population of just 20,369, Feltre is a quaint hill town in northern Italy, but the rigorous climate and persistent bureaucracy make it a less than ideal destination for many expats. While the Dolomites loom majestically to the north, the town's history is checkered, with battles, sieges, and foreign rule defining much of its past. The center was largely destroyed in 1509 during conflicts between the Venetians and the League of Cambrai, and it was later besieged by Austria during World War I. Today, Feltre maintains a 16th-century style, but the challenging weather and tedious red tape are likely to be ongoing headaches for those considering a move. This town is best suited for hardy souls undeterred by a heavy tax burden and administrative hurdles.