We have never purchased the trip insurance. And yes, we've traveled to WDW in February, from New England.
We don't get it because 1) the cancelation policy for WDW states that if you cancel inside of your 45 day window (for packages), you simply lose the non-refundable deposit ($200). If you purchase the insurance and have to cancel, you are out possibly more than that (the cost of the trip insurance is typically more than $200 for us)
Ok, so yes, it would cover airfare....well, we travel Southwest and if you cancel, you can use the airfare for a different flight...for us, we travel enough that we'd use that airfare no matter what, so again no loss for us.
Some people like the extra medical coverage provided...our health insurance covers us nationwide so we don't need that either.
All things to consider when thinking about trip insurance...and make sure you review the policy and ensure it covers whatever scenario you are hoping to cover...I've been in the insurance industry for almost 15 years and not all polices are the same, read the fine print.