Re: issues w/ travel plans - I’ve gotten stranded or left SOL before. My general course of action is to just buy a new ticket/room/whatever and file a claim on my credit card. My wife cracked the bumper of a rental. Chase paid. Flight got canceled. Polish air refused to give me a refund until 6+ months later after I had filed a complaint with DOT. I booked a new (more expensive) flight and Amex covered the cost.

I did get absolutely screwed once though. Turns out you can’t book a hotel in Paris after midnight because the system rolls the date over. Ended up sleeping on a couch in the lobby that night.