Yeah, that's the sort of thing that worries me.
Conditions for eligibility for the insurance may vary between banks & cards, but with a National Bank Gold Visa you're supposed to be covered if you pay at least half of the up-front travel costs for your trip with the card. Their brochure spends some time explaining what "up-front travel costs" are. Under that policy you wouldn't necessarily have to have paid for the rental car with the card, but you would have had to pay for
something with it: air fares, accommodation, etc.
It's obviously intended to get you to use your credit card, and there are quite a few reasons you might not want to, eg some travel agents charge a 2% surcharge for a credit card. (I don't know if they're supposed to, but they do.) So the "free" travel insurance can certainly complicate things.

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