My worst experience was getting our family (two small children) kicked off of an over booked flight during a stop over in Newark, NJ.
We did not volunteer to be kicked off, but were told we would be reimbursed $400 per ticket.
So, we spent the night at a crappy hotel in Newark, missing a day of vacation. Then we had to leave the hotel at 4am (two small children again), and take a taxi across NYC to JFK airport.
Finally, we were reimbursed $60 per person, based on the assertion that they had gotten us 80% of the way to our destination. After a lot of screaming, and pointing out that it was a *$%%#$^ good thing they hadn’t gotten us 80% of the way to London, and also that I’d rather be any on Earth than Newark or NYC, I got them up to $170 per. Still less than half of what they promised.
The airlines do indeed suck.
My worst was December. Our connecting flight into Chicago was cancelled (no plane) but not in time to do make the connection by driving. They bussed us to O'hare while they rebooked us through Minneapolis. No flights for us at all from O'hare to Denver until late the next day. They offered to put us on standby but we declined because we didn't want to check (lose) our luggage w/o boarding passes on and actual flight.
Ended up renting a car and driving from Chicago to Denver. We beat the only flight we could be guaranteed a seat on by 18 hours.
The airlines suck, but the government rules on them are a huge part of the problem.