Can we just chat about annual insurance plans?

I don’t have a super specific question. I just want to know what kinds of tips or experience you have for annual travel insurance plans.

I’ve insured lots of trips before. I have had to make a claim once - had to cancel an insured trip at the last minute because both kids came down with COVID and although I was inclined to go and just isolate in our cabin at the beach the doctor strongly advised against it and wrote letter to that effect for the insurance coverage. I didn’t have any trouble with the reimbursement from insurance. So anyway, I usually do insure my trips if they are expensive enough to be a hardship if I have to cancel.

This year my family is doing what feels like a LOT of travel. We have three out of state trips planned as a family, plus I’ve got one kid going to summer camp with her scout troop and the other going to the national scout jamboree. So I purchased a general travel plan to cover us for the whole year (March through February). Obviously I’m hoping I have no need to make any claims. :)

I’m just kinda wondering how it works with these plans. I know there’s a limit to how much can be reimbursed - if we had to cancel ALL our trips it wouldn’t cover them all.

But let’s say my kid comes down with a serious illness and has to cancel her trip to Jamboree. Just that one trip is like $2,000 including the bus ride to get there and back. Do these kinds of trips cover that sort of thing? I assume it also covers if she has a medical emergency while she is away from home.

What is your experience with these things? Did I make a smart choice?