Question regarding possible compensation: If I had a flight LGA-YYZ-YVR, and there were issues with both legs of this flight, are these treated as two separate compensation requests? Or is it based on the different of when you were supposed to arrive at destination and actually did?

Details:
LGA-YYZ was cancelled due to crew constraints. Was able to get rebooked departing from JFK-YYZ 3-4 hours later (and YYZ-YVR was also rebooked to later in the day). This rebooked leg, in turn, ended up getting delayed off the gate and missed my YYZ-YVR connection. I was rebooked by Customer Service desk on flight the next morning. (Side note, they said they couldn't retrieve my bags so I had to overnight with same clothes, no toiletries. Super fun!) All in all, I arrived in YVR approximately 24 hours later then originally booked.

Would this be two compensation requestions? First leg for crew constraints, second leg for missed connection due to delay? Or just one compensation looking at both legs?

Much appreciated!