First of all, thank you all who referred InsureMyTrip.com. I gave them a call and got a quote, so now we're evaluating it.
Second, I could've sworn I read some where, likely here, that said something along the lines of it costing more the closer you get to your departure date. After talking to a rep at InsureMyTrip.com, I figured out why. A large portion of it has to do with the whole pre-existing conditions waiver. With most policies, if you purchase your policy within 14 days of your initial trip payment, you get the waiver. Outside of that window, you don't qualify, or if you do, it's a HUGE increase to premiums. What the waiver does is it prevents the insurance company from looking into your medical history to look for a reason to deny your claim. If it comes to that, it can turn into a HUGE nightmarish headache as it's subjective to interpretation and you'll have to fight the insurance company on it. Then there's the job related cancellation clause. You can only purchase that if you get your insurance within 21 days of initial payment. There are a lot of things to consider. I had the rep give me a price quote for a policy that provides the pre-existing condition waiver and the premium was 246% more than without. It's a huge difference. Just something to think about. But to throw this into perspective, I don't believe Disney's policies provide pre-existing condition and job related cancellation coverage anyway, regardless of when you purchase the policy.
Another thing to consider is default coverage...for when the service provider goes out of business. I don't foresee that being an issue with DCL, but if you're booking your own excursions, that's something that'll need to be considered. They don't offer that coverage after a certain amount of time either.
With that said, those who went through InsureMyTrip.com what company ended up providing the policy with your trip? I know Disney uses Allianz and IMT also provided quotes through them, so that gives me a small sense of security but I found other companies are giving a better rate with better coverages.