Once I filed for travel insurance after my travel plans to Patagonia were delayed by a blizzard. Getting there required 3 separate flights and 2-hr cab ride in

Once I filed for travel insurance after my travel plans to Patagonia were delayed by a blizzard. Getting there required 3 separate flights and 2-hr cab ride in the middle of nowhere Chile, which cost like $200. After Kafkaesque paperwork my claim was initially denied. They said I didn't have my boarding pass from the 3rd flight (first 2 legs were Air Canada, easy to reproduce, but the third was some small, domestic Chilean airline with a barely-there website and a Spanish-only hotline). Who saves a boarding pass at the start of a 2-week hiking trip through the Patagonian wilderness? Why is that third flight stub necessary, since I'm asking to be reimbursed for the cab ride when I got there (which I have documented proof for)? I had to arrange for a conference call with a Spanish translator and the insurer (srsly), and eventually they paid up. But how many people go that far? It felt like the plot of "The Rainmaker". The only other time I had to use travel insurance was when I lost my brand new iPod while changing planes in Seoul, South Korea. Even though the insurance covered "lost or stolen" they claimed they couldn't reimburse me because I hadn't filed a police report with the South Korean airport police (it was the middle of the night, I don't speak Korean and I didn't realize it was gone until later). And why do I need to have a police report if it was lost? So I can definitely sympathize with how unscrupulous these travel insurance rackets are. That being said, I don't think asking him to fly home was that unreasonable. How are they supposed to validate the care he's getting there? He just going to dictate his care and hand over a massive bill from Singapore? But usually this involves taking them to court and getting a settlement.