This is a bad idea. The street scene has moved mostly online. If you do find street strollers, you're more likely to get caught in a sting, or worse, you'll be assaulted and robbed. Winnipeg's North End is so much rougher than Calgary's roughest areas. Without exaggeration, Forest Lawn, Ogden, East Village, and other rougher parts of Calgary don't hold a candle to the bad parts of the North End.
Stick to the options mentioned in your other thread. Winnipeg's small and it'll take you 20 minutes during off-peak hours to get to most places, even from St. Vital. For reference, it's a 19 minute drive to get from St. Vital to Emma's incall and 15 minutes to St. Boniface where you'll have more options. There are also some AMPs along the way on St. Mary's and St. Anne's.