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Last year I bought an ipod touch in the US and was able to register it to my UK account with no problem (while in the US).
I would suggest you open an itunes account for him in Canada. You can use your own credit card, then delete your card after the account is set up and add an itunes card. Give the account log in details to your Dad and he needs to make sure he is logging into the Canadian store.
I think it should work as long as he is in the Canadian store.
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