Great post, esquire!
I really only have two suggestions for Winnipeg as it continues to develop (that process alone will take care of all the others).
1. Enough with the Tyndall stone. The city needs some colour. No more beige buildings and pale concrete streets, unless you build the Maltese architecture to match. What you have now is great, and it'll make a beautiful and distinct core for the city's future, but it's time for more colour.
2. Build more bridges. The city has two rivers and only a handful of bridges. The only hardships I ever had commuting in Winnipeg were the bottlenecks around the bridges. Cities with Winnipeg's population should have many times more bridges. Even poor ones - Sarajevo, Bosnia, has more bridges per city block than Winnipeg has in total. And you could walk across its river.
Other than that, rapid transit wasn't even that big an issue for me. Everything moved very fast - faster then here, for example - except the parking lots the roads turned into around the bridges. Build more bridges and your perception of traffic problems will greatly decrease.
Oh, and one other:
3. Fuck the Globe & Mail. The Human Rights Museum is a beautiful building!
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Note to self: "The plural of anecdote is not evidence."
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