Vancouver is nice and scenic and the city has more money to work with (so better roads, buses, etc) but in terms of overall coolness, Winnipeg definitely comes out on top, in my opinion. Its more grungy, and that seems to bode well with the artsy types (case in point: Winnipeg's local music scene is way better than Vancouver's). It sounds like the comic is going to have a bit of a grungy vibe, so that would be my guess as to why she chose Winnipeg specifically