IMO, I can compare Winnipeg Transit to four cities- Calgary, Edmonton, Vancouver, and Red Deer.
Red Deer has the best transit system, but I am not sure if you can compare it to Winnipeg, as Red Deer has only 89,000 people. In Red Deer, the buses run in every area of the city, and go through Industrial areas. They all meet up Downtown, and you can get to where you are going very quickly.
Calgary, IMO, has a better transit system for one simple reason- the C-Train. The C-Train runs until 2:00AM, and connects all major areas of the city. The only problem with Calgary is the buses usually stop running around midnight (you usually take one connected to a C-Train station. Also the Southeast area of Calgary, where there bulk of the city's industrial area is, has inadequate bus service, although there are plans to build a C-Train through this area by 2020.
I did not have too much experience with the Edmonton transit system, and never rode the LRT, since at the time, it went basically from the University, through to the Northeast. Although they have since expanded the line south to 51 Ave, and are planning on building an LRT route that will connect to the West Edmonton Mall in a few years.
I only have limited experience with the Greater Vancouver Transit system, but the Skytrain is without a doubt, the best Rapid Transit system in Western Canada. The addition of the Millennium Line (runs through the North part of Vancouver/Burnaby/Coquitlam/New Westminster), and the new Olympic(?) Line, which runs from Downtown Vancouver, through to Richmond, and the Airport has only improved their transit. There is also a West Coast express (Vancouver to Port Coquitlam), and the Sea Ferry connecting to North Vancouver.
The only thing I dislike about the Greater Vancouver Transit system, is you need to purchase different tickets for different zones in the city, so it can be costly if you live in the outlying areas, and want to commute to Downtown. I know there was talk of Calgary eventually implementing a similar zone system, but it has yet to take effect.