I have a yearly travel insurance policy which is good for trips up to a month in duration (approximately $275.00 per year). You can go down south as many times a year as you would like, but you have to cross the border back into Canada at least once a month. When we were going to Arizona for the winter, we would stay down there for 5 months. So, what we had to do, was get insurance for all the days we stayed down there after the first month - it was approximately $10 per day (so approximately $1,200 for the extra 4 months).
We got our travel insurance here in Canada (including the extra insurance for staying there for the extra 4 months)
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