Glad to hear your first trips was (almost) successful and hope you have many more happy trips.
I don't think the extended warranty, not only Good Sam, but any extended warranty, will cover user error. That is an insurance resolution.
I had a similar experience with our first Pop-Up. The awning blew over the top of the trailer and punched a hole in the roof. Insurance paid over $4000 to replace the roof. On a pop-up, it wasn't just the outer skin.... it was the entire roof...the entire thing that raises up! Hard knock lesson learned about awnings. At that point in time, I learned to never leave them extended when not there. That was some 20 years ago now, and following my own advise, never had issues with another awning since!
Check with your insurance company. Good luck!