I live in Winnipeg, Manitoba.
1. I don’t have first experience about working in this field, but from what I hear, opportunities in this area are generally available...especially if you’re looking at entry roles.
2. The weather is great in summer, and one of the most brutal you will find in Canada in winter. There’s a reason people refer to Winnipeg as “winterpeg”. From talking with those in Saskatchewan, their weather is fairly similar in winter.
3. Taxes are high, but general living expenses are probably lower than other areas like Toronto, Calgary, etc.
4. Transportation System within the cities are generally adequate.