For our Feb '01 trip, we purchased the travel insurance.
Our flight out of Duluth to Chicago was delay due to "air traffic controller", which is a fancy term to too many planes in the air.
Anyway, we missed our connecting flight in Chicago, had to stay the night in a hotel, and catch an early morning plane the next day.
The travel insurance paid us for the cost of the hotel and our meal. We lost the points at BWV for a Friday night.
The travel insurance company want documentation to the delay, which I did get from American Airlines, but other then that it was pretty easy.
One thing to mention, we were only received the insurance because we were delay more then 12 hours (we actually were delay 12 hours 5 minutes), otherwise we would not of gotten anything.
I tried to get the value of the points paid also, but they wouldn't.
For our future trips, I don't believe we will do travel insurance. The limitations are too great for us.
Hope this helps...