Our TA suggested we add the trip insurance when we make our final payment. We weren't 100% sure when we booked, but I think we better get it since we're traveling with four small children.....just in case.
As a person who's used travel insurance quite a bit (and had to file two claims), I can tell you that you'd better shop carefully for travel insurance. There is a huge variance in the terms of the coverages. The important thing is to understand what the trip insurance does and does not cover.
Also, most trip insurance policies have deadlines for writing the insurance -- usually within a short time of making your reservations. If you wait until you pay everything off, you may find that you can't get travel insurance because you waited too long. Obviously, the insurance companies are protecting themselves against fraudulent claims.
I'm not sure who Disney uses, but DVC uses TravelGuard. I've used them a number of times and they are an excellent company.
NOPE.
This is our 3rd trip at this time of year, and we have never taken the insurance. If you read WDW's cancellation/change policy in full, there is very little that would not be covered under their regular policy anyway. To me, the chance is too slight to pay for the insurance. Of course, everyone's risk tolerance is different
Also, in regards to airfare I can definitely see where that would make sense but we fly Southwest anyway, so we won't lose anything if we have to cancel.