As a life-long Winnipeger (actually just a tad north in St. Andrews) of more than 70 years (I started following the Bombers in 1957.), I know the city pretty well and, in my opinion, Winnipeg is a city in decline. The decline has been going on for decades and was helped out by a previous mayor who did not raise property taxes for, what, 8 years and encouraged suburban sprawl. Anyway, apologies for the politics.
Good luck with your potential opportunities in Cape Breton, a beautiful part of the country.
I've got all sorts of friends and family in Calgary including my only grandchildren. We've been tempted to move but something about this place in spite of it's "aches and pains" keeps us here.
Cheers.