I have never signed a contract before in my life because I hate being locked into any one company for any period of time since I travel so often and I'm not in Calgary all the time for extended periods of time it just doesn't suit my lifestyle.
That being said, I also never haggled with the providers. I would just shop around for the best deal every so often (it's even better now with Wireless Number Portability) and if I found something better than what I had at the time I would just switch.
The biggest advantage is not being tied down for any period of time. To be able to bring your phone with you anywhere in the world and use that phone as long as they have GSM. In my opinion that freedom is more than worth any premium I have to pay for my phone.
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