I generally think trip insurance is actually a bad idea. I've only done it for cruises to cover medical evacuations.
Personally, to me, insurance is to cover the things you cannot afford to lose. I have homeowners insurance because I can't afford to lose the house. I have car insurance because replacing a car is a lot of money but more importantly I get a lot of liability and an umbrella policy because I'm afraid of the aftermath.
I don't buy insurance on an iPhone. Now, don't get me wrong...I'll be saying some very non-Disney language if I break my phone but it's really not the end of the world. I'll go buy another one. But I'm not going to spend $8 per month and then pay a $200 deductible for a phone. Same thing with WDW...don't get me wrong, I will definitely be saying some very non-Disney language but if you can afford to self-insure yourself then you're going to come out ahead....I mean, insurance companies come out ahead, that's why they're still in business.