Just a thing about mobilicity and wind, they run on AWS1700 so an iPhone is not compatible. If you are buying a phone out right you need to get one that is compatible with that band. So you'll have to buy a used T-Mobile phone from the US IIRC. Google's Nexus S, a bunch of Samsung phones or a bunch of HTC phones work.
I've bought phones outright before and depending on the contract it works out cheaper over the three years. If you're a person to use a lot of data, make lots of calls etc or you want a new phone every second year you are better off going that route. In any case, first thing I would do is complain to your current provider and threaten to quit, usually they'll put you through to retentions department and you'll get a much better deal. I pay ~$40/month with data now and it's worked out pretty good for me so far (but I'm stuck on another 3 year contract).
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