Flying back to Calgary from most of the US is not too difficult even if you have to take a connection. Visiting parents in Qualicum Beach on Vancouver Island is another story!
i'd definitely look at some smaller cities in the milliionish metro pop range. They are usually a lot more liveable and affordable, and businesses are often thriving. Cities like Tucson, Raleigh, Austin, Richmond, Colombus, and many others. ie, getting a house and a nice golf membership in a city like that is a tiny fraction of the bigger cities, and a lot of them have good culture, food and outdoor things to do.
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