Buy local.

A good LBS will include at least a year, sometimes more, of basic tune-ups when you buy the bike from them. Unless you do all your own work yourself, this will offset any possible price advantage you might get if buying the bike in the US.

As to which bike, there are numerous options. If speed (and the perception of speed) is not important: Surly LHT, Trek 520, Cannondale Touring. Maybe the Masi Speciale Randonneur.

If you're looking for something with a little more "zing" and want the option to ride on dirt and gravel (but not real off-road stuff), a cross bike is a good choice: Surly Cross Check or Traveler's Check; Bianchi Volpe; Jamis Aurora; Specialized Tricross.

If you're sticking to pavement: Salsa Casseroll, Specialized Sequoia.

Also, Marioni is a Canadian bike manufacturer that apparently makes some good bikes.