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Am I the only one who finds it odd, that OP is asking about what city is better to move to without doing any research about it before asking? I've contemplated moving to the island, and even before mentioning it to friends I had already been over twice on my own accord to "check it out". I spent a weekday and a day on a weekend in the town I was thinking of living in, worked out what stores and shops were there and how much mail-order I would have to do for things like my car hobby. I wanted to know about the housing market, so I went around for a day with a real-estate agent. It seems to me, the cost of taking two vacation trips to see what your living situation might be like is a small cost compared to being "stuck" somewhere you don't like for 5 years. Heck, I'd be pushing my boss for company-paid tour of both the Calgary and Toronto facilities.
I've been pretty careful to not comment on specifics about Toronto/Ontario, because the reason I call it "onterrible" isn't any reflection on why you may or may not enjoy it. In fact, there are things I definitely miss about the place. But overall they are minor and I still dread spending anything more than 3-days back there. But, that's me and I have very specific reasons why I feel that way.
It's not as simple as saying "if your career is the priority, go to Toronto", or "if you want to be close to family stay in Calgary". There are far too many factors. Lets take your after-work hours as an example. In an early post you highlighted the fact that Calgary being close to the mountains is a plus. What you may not realize, if you haven't spent time there, is that those mountains are good hour away. Calgary is FLAT. If, say, you enjoyed things like hiking, mountain biking, walking the dog, etc. You might actually enjoy living in certain parts of Toronto more than Calgary...because you can be out your door and in the woods in 5min. (SOME parts, not a generalization for the city). If, on the other hand, skiing and snowboarding are your priorities you'll find Toronto to be a joke. Small hills, rock-hard snow and lift lines that wrap around the lodge. If you're not a member of a private ski club, skiing in Ontario pales in comparison to the mountains.
If I were in your shoes, trying to make this decision I would do the following for each city:
1) work out exactly where I'll be working (address).
2) determine how long I'm willing to commute.
3) Using Google Maps, and the time-of-day function, start figuring out where in each city I could realistically commute from.
4) Using mls.ca start looking for properties I could purchase in the areas I determined from #3.
5) Using streetview and the satellite function 'drive around' the areas and see if I'm actually attracted to any of them.
6) Start reading the local newspaper for each city, and the communities that peaked my interest.
7) Go and VISIT each of the cities, testing my commute at actual commuting times to see what it's like. Spend two days in each (minimum) living as though I live there.
-Dave
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