> Even if I did try to contact a hotel in the event of travel disruption, I’d expect to be funneled into a labyrinth of computerized customer-service menus or AI doomchats before anyone could even try to help me out of my predicament.

This has not been my experience. Hotels, unlike airlines, are still quite hospitality-oriented. You can pick up a phone and talk to the person sitting at the front desk, and they will work with you (just don't call during check-in time). Hotels don't routinely overbook like airlines because then they have to pay for another hotel to house you.

Also when I book a hotel, I get multiple options for booking, some with no cancellation policy, some that can be cancelled before a week, and some that only have a day, being priced accordingly.