For example, Vancouver's real estate is pricey because it's one of the nicest places to live in the world. The rise of teleworking won't erase the mild weather all year round, the access to world-class mountain sports (hiking, climbing, cycling, skiing, etc.), the ocean with its views, great asian food, the rule of law, liberal culture, etc.
That's a very different scenario than, say, Winnipeg where it's -30 half the year and the other half the year the insects are so bad they send trucks around to fog pesticides. Plus you have conservative culture, no mountains nor ocean, little in the way of outdoor sports unless you like quad biking and fishing, or hockey.
I lived in Vancouver for a short while, and have visited Winnipeg several times for conferences and work trips. I can see reasons to live in Vancouver even if you didn't have to live there for work. I can see no reasons to want to live in Winnipeg unless someone was literally bathing me in money.
