Are you also a Canadian or a PR? how will you land in Canada? as a tourist?
If you're coming as a tourist then you can't work anyway and must apply for a work permit and find a job. Getting a job is not hard, depending on what field you're looking in and what profession. But if you have the proper experience and the employer is looking to hire then it's no problem.
Life here is really really good, better than most countries in the world with low crime (again depends where you live) and generally a good quality of life with decent health care and education. I live in the Capital, so I can speak from experience that you could be paying about 1000 rent for a 2 bed room apartment in a good area. Ideally you'll need about 3000 dollars to make ends meet but that's tight so maybe 3500 dollars is better (after tax).
As for best Cities, if you don't like the winter, then out west is best for you in BC or southern Ontario (Anything south of Toronto) where the winter mimics the American North east which is "Ok", not as cold and not as harsh as Ottawa or in the eastern side of the country and Quebec. The middle part of the country is coldest, so stay away from that (Manitoba, Saskatchewan and Alberta), their winters are worse than ours. However if you forget the cold, the best big cities are Ottawa, Montreal, Toronto, Vancouver and Calgary (not in that order but you get the idea), this in terms of job market etc.
How do I survive the winter? it's not so bad
you get used to it and with proper clothing you'll be fine. Every where is heated so don't think too much about that. We have 4 seasons which is really nice.
I hope I answered most of your questions and best of luck
