Winnipeg has lots of culture and history. largest french speaking population outside of quebec. Cool festivals and theatre. Incredible lakes just north of city.
However, crime rate is going through the roof. Not all over the city, but certain parts for sure. It's quickly earning the nickname as worst city in Canada. It's either a love/hate type of place. My brother is a business exec and is taking a lower position just to get out, if that tells you anything.
Weather sucks, mosquitos in summer, very cold in winter...you'll know from being in Wisconsin. My advice would be to avoid, but thats just my opinion.
Victoria is really quite cool. Lots of history to it. Warmest place in Canada. Home to either nearly deads or newlyweds.(I.E. very old or young couples). Great weather. Lots of sunshine. Very touristy.
Not sure about rental pricing, but housing to buy is very expensive overall. Good quality apartments, but you're paying for it. Big university with U Vic being there.
My advice is do a Van-Vic trip. Take the ferry from Van its quite nice.
In terms of Vic vs. Van, its two completely different cities. Van is a very large metropolis with all the wonderful things about a big city, but also lots of bad things. van has a lot of homeless, lots of drugs - google DTES (downtown eastside), you'll see what I mean
poorest postal code in canada.
Victoria is a lot smaller, but the jobs might not be as plentiful. Do a quick search to compare what's out there.
Also Vancouver is close to Squamish/Whistler - two of my favorite places in BC. Also North Vancouver has cypress mountain, seymour and grouse mountain. Skiing, hiking, etc.
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