What about 'stay protection' from your booking agent, like Expedia or Hotels.com ?

The first thing you have to do is read what is actually covered. That's the key word. It's usually not everything.

Then compare it to an independent travel insurance policy that will cover all of your plans rather than just the ones offered by that booking company.

I have an annual travel insurance policy so I decline any extra insurance offered by a travel supplier.

My private health plan already covers travel insurance, plus both my credit cards also includes protection with better coverage than what Expedia is offering.

Things I'd wonder about:

• What does the fine print say? Exactly what is covered for reasons for cancellation and interruption?
• Is $50,000 for emergency evacuation enough? It seems low to me.
• $10,000 for medical expenses may or may not be low depending where you are. I wonder if my little accident in London last month had happened in the US if $10K would have covered an ER visit.

I'm more concerned about catastrophic expenses such as medical incidents and think less about cancellation and interruption losses. If I didn't automatically have coverage for hotel and flight costs I'd doubt I'd buy it. The question I'd ask myself is if the thought of losing $3000 is uncomfortable enough that spending $150-300 takes away the anxiety.

re: evacuation coverage. Sometimes that means emergency evacuation to nearest treatment facility (i.e., ambulance ride) versus taking you back to the US.

I am a Booking.com devotee. I always choose the "pay on arrival option" with free cancellation that's typically up to 24 hours prior. The annual travel insurance policy I have should cover whatever happens if I don't show up.
(I do the same with airline tickets, not accepting the protection that pops up.)
It's a more expensive rate with Booking com for free cancellation, but with my loyalty "discount' it's about offset.
I would have qualms about a third party (including Booking.com) handling a claim.

The dates you are covered could be important. With my credit card insurance I'm covered from the day I fly to the day I return. If you only booked the hotel on Expedia would you only be covered for the days of your stay at that hotel? What if it's one of a few hotels on a longer trip?

The devil is always in the details. Read the policy fine print --TWICE. The med evac and trip delay coverages sound a bit low. The trip cancellation / interruption coverage also seems low -- how many trips actually cost less than the coverage amounts? You might want to look and independent insurers and compare the cost and coverages.