Moose Jaw, Canada

The population of 33,665 might seem quaint, but Moose Jaw is no sleepy prairie town. As an industrial hub and military flight training center, this city has a distinct blue-collar character. The long, cold winters and heavy bureaucracy can be a persistent headache, but the region's agricultural roots and scenic riverside setting offer a certain rustic charm. For those who don't mind the regional climate and can navigate the local red tape, Moose Jaw could be a viable option - but it's certainly not for the faint of heart.