Thank you for your reply!
I should have been clear, yes, I think CSR insurance should cover hotels booked with URs. For our upcoming trip I booked the air with URs and Chase said insurance applies to the trip booked with UR points. But they were not clear on the hotels booked with other program points.
I think I have never seen any reservation confirmations booked with points showing the monetary value. I guess it is reasonable, but makes me wonder about using free night certificate. My email confirmation shows "Free" for the cost.
I have used
Insure My Trip before, but did not know they have chat feature. Good to know!
BTW, it's good to talk to you again, wanderlust7!