Don't know if it will help anyone.
But quick TR with how it went with crossing the border.
Booked two Flights from JFK-BUF.
Flew to BUF, had a car pick them up from BUF Airport to cross the border, and take them to their final destination in Toronto.
Flight was a breeze, at the border they asked 212 Questions. Took about an HR at the border till they went in and out..
Needed them to show the rapid PCR taken within 72 hours and the antibodies test they took.
They required for them to take another test in the airport, didn't ask for insurance cards or anything else, so I take it that it was free.
And then they were sent off with another kit, for themselves to take a 3rd test in 10 days from the one's taken in the airport, and they would come pick it up in Toronto from them.
Flight was at 2:55pm and they got to Toronto at 7:15ish BH.
For the way home to NY a direct flight will do beH.
For those that will ask yes we all had a candian Citizenship card, we're dual citizens.