Toledo, OH, United States

The Toledo Strip is a commercial hotspot, but don't be fooled - living here comes with its fair share of headaches. While the Maumee River offers prime shipping access, navigating the bureaucratic tangle between Ohio and Michigan over this 468-square-mile region is a persistent challenge. And with the state's history of border disputes, a healthy dose of cynicism is required when dealing with local authorities. The climate is also a factor, as the Great Black Swamp makes parts of the city nearly impassable after heavy rains. Overall, Toledo is a place best suited for those with an entrepreneurial spirit and a high tolerance for red tape.