It depends on what insurance you buy. There are lots of scenarios people aren’t made whole. To reduce Hail claims in Alberta your policy will explicitly state the roof depreciation factor based on age.
On a car if it has significant damage is worth less money then a car that has never been in an accident. Your insurance does not cover the underlying value loss.
Or if you total you car and have a loan for more than the value or prepaid maintenance or warranty those things in general are not paid out. Just the value of the car, you aren’t entitled to the same car or even the ability to purchase the same car, just the underlying depreciated value. Or a lease down payment will screw you over in an accident scenario.
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