Travel writer in today's WSJ wrote a pretty long article about travel insurance in which she strongly comes down on the side of getting it after going without for many years. Found a few examples where it definitely paid off for the policy holder.
Also found a AAA travel agent who said half her clients get insurance and for the others, she makes them sign a waiver acknowledging that they are skipping it.
Because it's hard to give and get actual quotes without knowing a person's particulars, she basically said to shop with Squaremouth. Which is what I've done my past several trips. There's also Insuremytrip.
She was very pro medevac as well. Remember that Medjet has a AARP discount but also an age ceiling.