This can work a lot of times to your advantage and I do agree that this is especially good if you plan a vacation a long time out. You can just buy the cheap seats knowing you can get the money back for future flights.

But you also need to consider that Southwest does not have same day standby. So if you want to catch an earlier flight and even if they have seats you have to pay the ticket price for the then going rate (usually the most expensive). I ended up paying a couple times the full rate just to get home 4 hours earlier.