De facto, he is single. The same case is with children. If they are not with you in Canada, you claim that you don't have children in Canada. I am not claiming it's correct, just wonder.
If you have what's requested, just provide it. If you can't do that in time, request an extension with explanations and proof of your efforts to comply. .
Sorry, it's correct and confirmed. Border officers are humans not machines. I have lots of examples of people crossing with a bag full of insulin without any issue with 1-2 year supplies. When people move in to Canada, they panic and bring a lot of medical supplies very often, never saw any...
You need also think about how to measure glucose if you use test strips. They maybe completely different from the ones she uses in her country.
But FreeStyle Libre Sensor is available at any drug store and may be covered by the insurance.
Carry on bags are quite big for a 4 months supply, definitely. And you can use different types of cold agents to maintain their temperature. And 22 hours is not an issue.
You can check it in but it's risky. As it can be quite cold in a cargo hold, even below zero. But modern planes usually...
Yes, she can bring as much as she needs and more. Just have some paper from her doctor, just in case. Most likely no question would be asked at all. Just don't put it into check-in luggage, you should put into a carry-on to keep it in the cabin and prevent it from freezing.
You need to meet one of the following criteria to be able to apply for BOWP:
have a valid work permit
have an expired work permit but maintained your status as a worker
be eligible to restore your status and get a work permit