Should you buy trip insurance?
If you think you need to, them buy it, if you don't think you need to, them don't.
Should you buy an annual travel insurance policy if you dont travel often or should you buy insurance on each trip?
Annual travel insurance is a much better option, even if you don't travel often. Buying insurance each trip is much more costly.
If you are an American traveling through Canada with no health insurance should you purchase health insurance for your trip?
no you will need green cards after two years
If you're insurance coverd u for 30 days would you still be covered if you've no intention of coming home within 1st 30 days and then bought a single trip cover for rest of trip?
177.83 kilometres (110.5 miles)
Does trip cancellation insurance fall under casualty insurance?
There are too many variables to provide an answer here. The best way to find out is to contact a local agent or agency and ask for quotes or at least a ballpark estimate.