We are travelling internationally in May. Given that we do want to purchase trip insurance, how do we go about finding the best policy? A family member used Squaremouth several years ago. Is that still the best way to go about it?

Here are the facts:
We are using AA miles both ways, and all hotels have 24 hour cancellation. The only real expenses paid in advance will be about $1,000 for shorter flights.

Lastly, in what order shall I make the purchases? I have not yet bought the tickets for the smaller flights. Shall I buy those first, and then get the insurance a short time later, in order to cover pre-existing conditions?

How about medical care, and medical evacuation. Should I just get the policies with the highest benefit?

Thank you in advance.