I've come across a few such stories.
Overbooking airplanes means someone might be stuck sitting in the terminal for hours. Overbooking.com means someone might be made to drive around late at night, tired, with nowhere to sleep.
It also might mean you miss getting somewhere in an emergency, like visiting a loved one before surgery. And it also might mean you miss things you couldn't miss, like a job interview.
One of the worst memories of my life started by missing a flight (and it wasn't my fault).
[1] https://www.nytimes.com/2019/02/18/business/hotels-overbooke...
It sounds petty but having paid for a room, being exhausted from a Pacific flight and being moved to a hotel twice the walk from the conference (important if you're going to be back and forth all day) was mildly annoying.
I'm not 100% sure - but the one time I was walked I had picked the cheapest available room. You know those bullshitty-looking price differences where you can book on floors 9-11 for X and floors 12-14 for X+5? I suspected I had signalled my place on the hierarchy by picking the cheapest room available. Subsequently, especially while on an expense account (sorry, Intel! :-) ) I always picked the ever-so-slightly more expensive room and have never been walked again, even in the middle of conference season. This may be bogus reasoning, of course.
I have trip this coming month through Expedia and the last leg of our bargain basement flight got cancelled. The rep told me there were no flights for days surrounding our original flight date.
I had to sit on hold for a long time but I have to say they were great. United swept our transportation out from under our feet but the rep was able to wrangle a flight with fewer stops that arrives earlier without us having to pay the difference. We had those locked-in cheap tickets that charge you a couple hundred just to upgrade your ticket before the price difference is even considered.
Needless to say we were greatly relieved...
Another example is Marriot will commonly let the local management control inventory. They commonly use the cheapest room to book to max capacity and upgrade people until they are fully booked. It almost never makes sense to book a more expensive room unless you are booking within 30 days.
I would say most of these cases, the renter wouldn't have a car. I've been stuck in cafes after booking/Airbnb scams