CIBC Aeroplan Credit Card Insurance claim - anyone have some expertise?

Hi everyone. Booked a flight through Cibc credit card. It was supposed to leave at 6pm tonight. But now delayed to 8:50pm. We won’t make the connection to Toronto and the one they’ve put us on will arrive 6hrs after the original one. Wondering if I’m able to claim for a hotel stay during the now long layover due to the delay?

If they end up cancelling this flight they keep pushing, can I just book another flight and claim for it after the fact? I’m seeing a direct flight tomorrow for $2k for both passengers. Just want to make sure I’ll get the money back before I pull the trigger