Years ago American Express had an annual policy for well under $100 for basic coverage. I renewed it every year until it was discontinued. Since then I've only had insurance when it was offered at modest cost when purchasing a long-haul flight, as it sometimes is, or when I've bought multi-continent tickets from the consolidator I use (Airtreks), as they include insurance at no additional cost with every purchase.
In all the years I've traveled I've never had occasion to file a claim, although I realize that could change at any time, especially with looming decrepitude. But it's yet another reason to spend time in the countries I love most in Asia where medical services are astonishingly cheap, such as a hospital visit I made in Bangkok and received a bill for $28 including 2 prescriptions.