We flew SW last month to/from PDX/MCO (Portland to Orlando). Our family now refers to it as "The Great SW Cluster of June 2021." Despite describing it as a "cluster", I still willingly booked additional SW flights, so clearly it was bad, but not BAD.
When we booked, the trip each way had 1 lay-over with plane change. Then, a few weeks before our departure, they added another stop (but not another plane change). PDX - DEN - MCO became PDX- DEN - OKC - MCO. Annoying? Definitely. End of the world? No. But still annoying
It got us into town about 90 minutes later than we had originally planned.
The way home was started as MCO - DEN - PDX. Then they added a stop at OHR a few weeks ahead of time. No biggy; again, no additional plane change. But then when we got to OHR, they basically said, "Guess what?! Everyone's getting off here! This flight is CANCELLED!" And there began our "adventure." First, they didn't tell us *why* the flight was cancelled, just very vague. Turns out there was bad weather in Denver, some sort of computer system issue, and (most importantly and most frustratingly) the pilots had hit their flight time limit for the day. (Seriously, how could they have not known this ahead of time??) Then it took them an hour to get us rescheduled. Then the arriving plane was late, and they were attempting to board 3 separate flights from the same gate; it was under construction, and standing room only, for 3 flights of ~145 people each. Lots of confusion there! Then they sent us to PHX, where we were delayed (again!). Of course, all this happened at inopportune times, so our dining options at OHR were snack carts, and when we got to PHX at like 9:00pm, nearly everything was closed as well. Originally, we had planned to get in to PDX (final destination) at 8:15pm. Hub's 78-year-old mom was going to pick us up, and is usually in bed by 9pm, so she was already staying up a bit later for us. By the time we actually got to PDX, it was after midnight. Poor lady was up to nearly 2am. Ugh!
My old flight pattern from PDX to LGB (about 20 miles from Disneyland), was PDX - OAK or SJC - LGB. Now, it's PDX - LAS - LGB, adding a chunk of additional time. I used to be able to do a "quick" day trip to Disneyland (it was about 25 hours from bed-to-bed). Now, I have to plan actual flight days, because I can't count on SW to be on time to get me to or from So Cal. Ugh.
All this considered, I've learned to just not look much at the emails from SW, ha! I double check that it's not something super-major (different airports, or hours different), and then only look at it otherwise like 48 hours ahead of time to get the updated times. Everything I've heard is that it's not SW-specific, but it's definitely gone downhill with SW since pre-pandemic.