So I was in the same boat. Our trip is 2 weeks away. Since we are renting the points for a stay at the Poly, we are not covered by any of Disney's cancellation policy's, nor is there a refund policy in place with the company we rented the points with. Our park hoppers can always be used another time (so no fear on losing that money), and the airfare should be refundable or movable in a worst case scenario. However, when I saw how bad this month has been I began to worry and did purchase travel insurance, but I purchased it last week. That doesn't cover me from Irma or Jose, but it should cover me if there are any other "named" hurricanes that could disrupt our trip. Per the fine print, they may not cover hurricanes if the storm had already been named at the time of purchasing the insurance. I am only covering the cost of the hotel and the airfare, so a plan for 4K. The total cost for the insurance was $147.00.
While I don't think that we will need it, I actually feel better knowing that we should be covered in the event that another event takes place. Watching the NOAA website, there does seem to be a yet to be named storm brewing in the Atlantic, and who knows what that storm will decide to do. I cannot tell you what I think is best for your trip, or your family, but I did want to share with you what I decided to do, as it looks like we are both traveling the same time (9/23-9/30).