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if you're highly skilled as defined in nafta a work permit will be no problem... you'd have to check if you meet the tn2 status. nafta made it pretty easy for US and Canadians with skills to get back and forth across the border for work. If you're not then expect a huge hastle. If you have US business interests you might consider just keeping property in Canada without getting citizenship.
Kitsilano by the beach is where you want to be if you have a little money.
cheers
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