It's all relative.
I had a 7:30 AM flight from LGA-DAL on Saturday that circled Dallas for over an hour and had to divert to HOU due to low fuel. Then we were stuck at HOU for a few hours with very little info being provided other than "we're waiting on the paperwork". They allowed people to deplane to get some lunch. Just when I was going to rent a car to drive it, they announced that we are reboarding. Then, it was an almost 2 hour delay at the Jetway because they couldn't make the PAX count match prior to when we deplaned. (Maybe some people were flying LGA-DAL-HOU?) I landed in Dallas at 4:30 PM while all scheduled HOU-DAL flights from 11 AM - At least 3:30 PM had been cancelled due to the pileup. By the time I arrived in Dallas, the weather was fine. So at least the 3:30 PM flight could have gone and the 2:30 PM flight would have been OK with a delay. (Air traffic aside)
All of this was due to weather, which is completely outside of SWA's control. But, in the moment, you can't help but get angry at the lack of info being provided so you can continue your plans. If we weren't leaving, I needed the option to rent a car to finish the journey or rebook HOU-LGA, which was leaving in a few hours with only a couple of seats left. In the end, I burned 24,000 points for about 20 hours in Dallas. But, at least we got there. That would not have been the case with AA, who would have cancelled the flight and offered me another one the following day.
But, I've had true bad experiences with Southwest too. Several months back, I was flying the LGA-DAL route again with a 7:30 PM departure. At 2:30 AM, they told everyone that they could get us on the 6 AM flight in a few hours. I declined, booked that 11 AM departure and went back home. The delay was due to mechanical issues and then the pilots running out of time and finally the FAs running out of time. Southwest knows their schedule. If this was going to be an issue, surely they were aware of it hours before they called it. I got absolutely nothing in compensation for the troubles. On the way back, almost an identical issue. Got delayed until 11:00 PM on a 7:30 PM departure. Only, they ended up canceling the DAL-LGA flight completely and making a new flight that landed at EWR. Well, that's quite a trek for me as I live 25 minutes east of JFK. We were told by the gate agents that we could send our info to Southwest and they would reimburse us for the travel. Fair enough as we would be landing in the wee hours with no traffic. 1.5 hours, and a $230.00 Uber ride later, I was home. I called Customer Service the next day and, of course, they denied responsibility for the travel. As this was a business trip, it wasn't as big of an issue because I got reimbursed, but it pissed me off that they told me a bullshit story to maintain order at the airport.