I think the key is WHY. As others have said, if you Live and Play outside the city then it's one thing, but if you're only going for the cheaper housing then you have to consider that the increased vehicle costs REALLY add up.
I just moved from a smaller community outside of Red Deer to right inside town. My daily Kilometer Toll went from 110 to 6. I don't care that the mileage goes to crap in town, I'm doing less than 5% of the Kilometers, factor in Oil changes, useful life of the car etc. and it doesn't take long to rack up considerable $$$.
A couple of things I'm loving... if I need groceries, want to go to a movie, etc. I don't have to book an hour plus for travel (round trip). + Small town amenities suck. You get a lot more in terms of public works in city vs a small town.
Keep in mind too, that while the extra dollars you would spend on housing in Calgary may seem like a lot right now... you'll get that back when you sell the house. Money spent on fuel and vehicle maintenance simply disappears.
Make sure you're comparing apples to apples with your commute. If you can leave for work early and get home early, you'll still be there sooner if you live closer. Don't make the mistake of comparing a Sunday drive out of town to a hectic rush hour logjam to a Calgary house. Plus make sure it's right to the road you would like to buy on, not to the off-ramp.
One thing to consider might be to buy a place in Calgary, and rent it out while You rent in the small town you're thinking of. This way you get to buy now while the market is down and you SHOULD be able to rent it out for more than a similar place in a small town rents for. If you decide after renting for a while that you really like the small town life and commute... sell the Calgary house and buy in your small town. But if you don't like small town life after a year then at least you're not stuck with a hard to sell house in a little town (which is exactly where my brother in law is)
Just my 2 cents, good luck!
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