If you're looking for service "almost anywhere in Calgary/Alberta", I would choose Bell or Telus...Rogers has major problems with their coverage, you might not have coverage if you live in certain parts of South Calgary or certain parts of NW Calgary. Don't know anything about Fido...
When it comes to phones, unfortunately, the most versatile phones are sold by Fido & Rogers (e.g. BlueTooth phones, ease of transferring address books, etc) - mainly because they use GSM technology. Fido & Rogers phones usually have more bells & whistles...
One more thing on phones, if you look at Telus/Bell/Fido/Rogers websites, they try and sell the "bells & whistles" of the phone (who cares you can download ringtones if you can't use it to make a phonecall!!)
I would suggest reading the reviews on phones, talk to friends to see how their phones work and then go to a store and ask to try one or more phones (ask the clerk to call a service number on two phones and see which phone has clearer reception)...
Here's some websites which might help you:
www.comparecellular.ca
www.howardforums.com (forums on all the major providers, you need to register if you have questions, but it's free and there are interesting nuggets of information here)
www.howardchui.com (review of phones, but a large number of the phones are not available here
www.geckobeach.com (website which has reviews of cellphones)
Good Luck...