Hmm, does the Chase insurance cover Trip Delay?
The current benefits guide spells out only four specific Covered Hazards for which you can claim up to $500 in trip delay reimbursement: equipment failure, inclement weather, strike and hijacking/skyjacking.
I've updated the wiki to reflect the more specific language, otherwise all the other information is up in the wiki post (6 hour delay coverage on CSR vs 12 hours/overnight on CSP, etc).
The key events that have been happening in recent weeks that would
not be covered are things like crew timeouts, or flight cancellations due to inadequate staffing. For those events you are basically stuck with whatever compensation the airline gives you.