Last year we did purchase the trip insurance for our trip in February.
We ended up missing our connecting flight in Chicago, which forced us to spend a night there, due an "Air Traffic Controller Delay" (fancy words for too many planes in the air).
The insurance reimbursed us for our hotel and meal costs, but not for our points. They explained to me that only a medical condition would allow for your points to be reimbursed.
We also got lucky that our delay was 12 hours and 5 minutes. If our delay had been less then 12 hours, we would not have gotten anything from the insurance company.
I must say that the insurance company was easy to deal with and did pay us promptly.
Do to the limitations of the plan however, we will not be using travel insurance in the future.
Hope this helps...