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I'm a Canadian citizen with permanent residency in the US and married to an American citizen. We would like to retire in a couple of years and spend time in both countries with family members....how do we go about doing this? Can you give me any advice?
Sounds like you have the immigration portion of things nicely in hand, assuming your wife has PR status in Canada. If not, she is still eligible to be in the country for up to 6 months.
Are you currently in residing in the US or in Canada?
If you're currently eligible for your provincial health insurance, my suggestion would be that you don't let your eligibility lapse. Socialized medecine may not be the absolute greatest, but it can come in handy at times.