when you enter canada, have customs stamp your passport. the stamp acts as your 6 month visa. if you leave and come back, your 6 month clock starts all over. insurrance is a tough one. I would suggest getting a policy from the states with a good travel ryder on it. make sure you read the fine print to be positive it covers you for everything. also keep in mind that canada doesnt recognize private health and they collect all payments up front from out of country patients. believe me it gets spendy real quick, so set aside a couple grand for emergancy because if your banged up bad and have no $, they'll try to ship you to Bellingham.