I was there in October for Matthew. We stayed at Pop and did not have travel insurance. We were already scheduled to stay thru the storm. We met people at the hotel that did have travel insurance and were glad they did because they could not fly out for a few days and it covered their hotel stay.
We did lose one day in the park when they closed. I went to guest services the next day, and they gave us each a 1 non-expiring pop hopper. Very gracious and appreciated.
With that said, I would not hesitate to return to WDW in the fall, and I would not purchase trip insurance. It just doesn't happen that often....