Yeah the cold and mosquito BS gets old. Thanks to El Nino(weather phenomenon, not the hockey player), we barely have any snow so far and will still be in +C temps well into December. Late December into January usually gets very cold for a couple weeks during normal winter years, but it doesnt last and ill take it over the mountains of snow they get further east and west of us. We have the warmest and sunniest summers in Canada with many days over +30C, and i barely notice mosquitos anymore(the city has done a great job of prevention over the last decade+). People seem to think its crime ridden but 99% of the time its drug dealers/gang members killing each-other, and every city has places that you dont walk around in at night. Its no worse than other cities the same size. We have an amazing food scene here too that rivals and even surpasses much bigger cities. Its also a very affordable city to live in. Im firmly middle class and my new home will be paid off before i hit 60. In Toronto or Vancouver it would be a million+ and i'd be making mortgage payments until i died. Winnipeg gets a shit rap. Its a great city.
As one who's lived and worked in both Winnipeg and Southwestern Ontario, I second everything you say. I don't think it's just nostalgia for my own home, that I feel Winnipeg is better in almost every way than this part of Canada. I'm not even in Toronto or the GTA and the average detached home price around here is around a million (it was $1.2 million before the interest rate hikes). If we'd stayed in Winnipeg we would have paid off our house years ago. As it stands the only reason we can afford the house we have is be bought it many years ago when prices weren't so bad around here (I live near Kitchener, ON).
My whole career I've worked as a criminal lawyer, both prosecutor and defence over the years. I can verify that 90% of Winnipeg's crime happens between gang members and in a specific area. The vast majority of the city is extremely safe, to the point that there is a noticeable difference in the competence of police officers who work in Downtown and North divisions versus other areas simply due to experience (or lack thereof). Aside from certain areas, Winnipeg is probably better than some cities its size ... I certainly felt safer walking around Charleswood or Fort Garry at night than I do in many places around here.
Food/restaurant scene destroys southwestern ontario. Very hard to find a great restaurant here, they're all mediocre in my experience. In Winnipeg its hard NOT to find a great restaurant.
What you say about winters is news to me. When we left Winnipeg in 2008 it was still full-on winter with snow and well below zero temperatures from Hallowe'en til Easter. That's been the #1 reason my wife doesn't want to go back because she felt trapped inside the house with the kids 6 months of the year. If the climate has changed that much in Winnipeg (in southwestern Ontario it's exactly the same now as when we moved here in '08) we may have to revisit the concept of moving back. If mortgage rates don't drop we could easily be forced to sell our house when we have to renew in 2025 and if we need to sell, maybe just go whole hog and return home.
Also people are friendlier and more down-to-earth in Winnipeg. I've NEVER been able to fully adjust to southwestern Ontario or make the type of solid friends I had in Winnipeg.
EDIT: Forgot to add ... in Winnipeg you don't need to worry about spending hundreds on rust proofing every fall only to have your car still rust out within 10 years due to the stupendous amount of salt on the roads in Onterrible.