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This sounds like just what I was looking for! What company were you able to find that was willing to insure a US registered car? Was the insurance contingent on you heading for PR? I'm going to be a TR for two years and was hoping to avoid the whole switcharoo to Canadian...

Sorry to wake up an ancient thread, but does anyone have experience with this? I'm in a nearly identical situation, moving USA (Boston) to Ontario, for two years on an open work permit off my spouse's study permit. I've gotten confirmation that Ontario is fine to let me use an International...