For US travellers
www.insuremytrip.com has a useful feature where you can compare a variety of companies' policies and their features - and the telephone agents I have dealt with are extraordinarily knowledgeable and helpful.
Don't know whether they do Canada, but their website might indicate a Canadian affiliate.
As for people's doubts about the wisdom of travel insurance - well, it may depend on your age and health (and the age and health of relatives for whose sake you might have to cancel a trip), the cost of your travel, and the bona fides of the insurance company you deal with.
I have several friends who had invested in trips of a lifetime, who suffered major medical emergencies mid-trip. Their insurance covered all but about $50 of the medevac, hospital and surgeons fees, hotel for traveling companion in the city not on the original itinerary, and the flights home, and returned a fair amount of the cost of the unused portion of their trips. Yes they could afford the trip, but they couldn't readily afford to restart or complete the trip later. If you just have a roundtrip plane ticket, some train tickets and a bunch of hostel or airbnb reservations to worry about, you may reasonably decide to assume that risk yourself instead of paying someone else to. To each his own and YMMV.