Sorry to hear about your travel troubles. I would suggest writing a letter to customer service explaining what happened; however there is no guarantee that the airline will provide any monetary response for either mechanical or weather related issues.
Regarding mechanical issues, the airline has to operate as safely as possible. I have also been delayed on an early flight out of a smaller, non-hub airport. Although grateful not to be on an airplane that did not pass a pre-flight checklist, it is painful to wait while they fly either a new plane or a mechanic and part in from another airport. No airline that I know of keeps all parts at every airport, and all mechanics cannot fix every issue. Some have more experience than others. But I knew it would take a fairly long time and in a smaller airport on the coast, it meant the long wait, so I said to myself that it was better to be on the ground with a problem than in the air with a problem. The airlines want to keep planes moving but they do not compromise safety which means preflight checks every flight.
going from one coast to the other on Southwest, the low cost, short haul carrier, they do not have a lot of other choices than to send you on different flights with a lot of stops when the long one-way is cancelled. I know it is not the best choice but the other option might have been wait until the next day (and there may not have been any seats left). I had a relative who was stranded for a week because their flight to Iceland was cancelled on another airline, so they just had to wait for the next flight. That airline only had one flight per week. It can be a potential flight delay vs price trade-off when something goes wrong and gets delayed.
As a person who flies a lot, I can tell you that delays and bad flights happen, but safety has to come first. If you write into Customer Service explaining what happened, they may choose to reward you with a travel voucher for future travel. Go to the “contact us” webpage for the address. I would suggest writing rather than calling because (1) it is a busy time of year and (2) it allows a customer service representative to see that you took the time to put something together because you felt strongly enough about it to write and (3) they have more options than the phone reps.
Some people get upset enough that that they never want to fly a specific airline again, so if you do not want a travel voucher, but want a refund on a non refundable ticket, I suspect you will be out of luck. The terms and conditions of a nonrefundable ticket are that the traveler will accept mechanical or weather delays. The pricing structure is not unique to Southwest, and it helps all airlines keep prices low.
I understand your frustration and I am thankful that delays were the worst thing that happened. Writing into customer service would be my suggestion — outlining flight numbers, cost, confirmation numbers, locations and dates — as your best chance for some sort of compensation.
Best of luck and I am sorry that you had the problems; although as an experienced traveler, I have experienced it myself and I understand how and why it happened based on the business model of keeping price low and the FAA regulations for passenger fares.
