There's an End Homelessness event at the beginning of December for anyone who may be serious about dealing with the issue:
https://endhomelessnesswinnipeg.ca/
Of course there are several organizations that try to deal with the various causes and effects of homelessness, including End Homelessness Winnipeg, Main Street project, Siloam Mission, Canadian Mental Health Association, Resource Centre for Youth and St. Boniface Street Links.
In addition both the City of Winnipeg (encampment strategy) and the Province of Manitoba ("Your Way Home") are working to try to alleviate homelessness and it's negative social and economic effects, but they are fighting a severe lack of affordable housing, general lack of good paying jobs with benefits, the lure of crime and substance abuse, and let's not forget outright hostility towards people some folks love to dismiss as being unworthy of assistance.
It's great that people here want to see and end to homelessness. I know many of us support the difficult but necessary work being done in this area.