I have to travel around the country a good bit because my kid plays high level kid hockey. I think we did 16 or 18 flights this year. Most were American and a few were Southworst. Unfortunately, there is no way to carry on a full hockey gear bag and a stick bag - he is 6' tall at 14, and uses senior adult size sticks with extensions. So we have to check baggage every flight. We always travel a day in advance and leave a day late. consequently, a delay or cancellation does not usually affect the trip and the extra day generally ensures we can overcome any misrouted gear issues. It costs me a bit more on the hotel bill, but we use the time to explore the destination city and I also like to use the time to hunt for allocated bourbons.
Honestly (knock on wood), we have not had many negative experiences, and most of those were not that bad and happened on the way home. Once, our last flight from DC to RDU got cancelled, so they gave us hotel, taxi and meal vouchers and 10,000 travel miles and got us on the first flight out the next day. Coming back home from Detroit in January, they bumped the hockey gear and it did not get to RDU until the next day. They put it on an Uber and dropped it on our porch that afternoon. It was mildly aggravating, but not really a problem. I think the key is just to avoid cutting it close if your time is critical.
Honestly (knock on wood), we have not had many negative experiences, and most of those were not that bad and happened on the way home. Once, our last flight from DC to RDU got cancelled, so they gave us hotel, taxi and meal vouchers and 10,000 travel miles and got us on the first flight out the next day. Coming back home from Detroit in January, they bumped the hockey gear and it did not get to RDU until the next day. They put it on an Uber and dropped it on our porch that afternoon. It was mildly aggravating, but not really a problem. I think the key is just to avoid cutting it close if your time is critical.