I was born and raised in Canada and have been all over the place. I will try to give a small description of the places that I have lived over the course of my 20 years.
Winnipeg, Manitoba: Born there in 1983. I spent 5 years there, so I dont remember a whole lot, but return visits have refreshed my memory a couple times. Winnipeg isnt the nicest place, but it has its nicer areas. Most of the downtown is quite old, but traditional. In terms of climate, the summer scorch and the winters freeze. Imo, I don't care for both extremes.
St. Albert, Alberta (near Edmonton): A booming city with a lot to do. Very beautiful environment and surroundings. Great people, great overall town. the weather is somewhat similar to that of Winnipeg. I lived there for 8 years, from age 5-13. I would recommend this city to you for sure.
Prince Rupert, BC: A rather small town with a population of about 16000. There is not much to do in this town, but it is green all year long, mainly due to the fact that it is literally the rainiest city in the world. no joke. There are only 2 high schools and downtown consists of 3 main streets. That should give you an idea of how small the place is. I lived there for 5 years, from age 13-18. graduated there and everything
Calgary, Alberta: I lived here for a summer, moved to Vancouver for a year and moved back. Calgary is by far the most enjoyable place that I have ever lived. In terms of people, activities, scenery, and overall grandeur. It is not very crowded for such a large city, (approx 2 million inl surrounding cities) and it is very well planned. Weather is very reasonable. The winters are cold, but not unbearable and the summers are gorgeous. The only thing is, is that you can have any sort of weather on any given day of the year, but that really isnt so bad. Finding work in Calgary is so simple its not even funny. I see no reason why there are homeless people here because of the abundance of manual labour positions available city-wide. I recieved 3 phone calls the first day that I was passing out resumes and I started work the next day
I highly recommend Calgary to you, if you are in search of relative calamity and peace of mind. There are a lot of nice areas to live in in all divisions of the city.
Vancouver, BC: I lived here for one year while attending school and learned a lot about the place. Vancouver is very crowded and very oriental, not that there is anything wrong with either of the two. It did not really suit my tastes as a convenient place to live, learn, or work. Finding jobs there is extremely challenging unless you want something simple like a grocery store, or unless you have a college education. Vancouver is a very busy place and traffic is quite horrendous almost all of the time. The older parts of the city have very narrow roads, which are just waiting to cause accidents. A benefit could be that there are a lot of surrounding cities and districts, such as Surrey, Burnaby, Coquitlam, Richmond, New Westminister and others. Living in any of those surrounding cities will not be as crowded and you will still have easy access to the larger city of vancouver. Another benefit is that it is close the the beautiful Vancouver Island (you may want to consider Victoria, BC also)
(no, i'm not just hyping up calgary because i live here. its worth it. :P )