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You make Winnipeg seem like hell on earth. True, the winter is cold, and takes some time getting used to. However, it's a great place to raise a family, and there are a lot of benefits to living here that not many cities have.
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the point is this.... if you were a young professional making high six figures or more, could ply your trade in many cities and had your choice of locations where would you rather live? A bigger city with more entertainment options, amenities, with a more temperate climate or Winnipeg? Winnipeg will be by far the smallest city and more so it is fairly isolated, there is nothing within 3hrs by car that can provide any extras. On the upside every player will be a celebrity and be adored where ever they go. If that is what the player wants that could be a perk too, but there is a pretty big downside.