Trip insurance is a difficult thing to figure. You need to consider just what is covered and what the chances are that you'll need it.
If it's hurricanes you are concerned about - remember that most airlines will allow you to reschedule flights at no cost if their schedules are affected by the hurricane. Also remember that WDW has closed due to weather only one day in its history.
So consider;
What are the chances that you'll actually miss your trip?
What are the chances that you'll actually be out $$$ if something happens?
How much is that worth to you?