Southwest is the largest carrier in our area, and what is great about them is that if you book and later the prices come down you can rebook ant get left over monies for travel credit within a year of when you first booked. This means that if it's a price we can live with and Southwest is our best deal we book right away with no risk. If you cancel or change too you have the same change policy, making it pretty low risk, especially if you fly pretty regularly and know you'll be able to use the travel funds.
I have that SW premier credit card too and am amazed at how quickly I accumulate freebie trips, a very fun perk. And when using points any changes or cancellations those point just go right back in your account -- pretty cool and risk free. Doing the math between this $99 card and the no fee card I was using regularly, the better perks not including the initial incentive made it worth it for me to get the fee card. And that initial 50,000 promotion was a decent incentive to bother to switch cards. // I haven't done what the previous poster said -- close and re-do and charging enough for the companion pass. Just saying it's a pretty decent card even if you just hold and use it. Never thought of doing what previous poster said. I tend to use just one credit card for the most part (paying off balance each month), but typically keep a second one too, just in case first would be lost or stolen or put on a credit card hold due to unusual purchase. Second is there just in case.
quagmire0 is a much for savvy user of credit cards than I am lol. Quagmire0 -- I'm impressed.
Only thing you have to do is pay the annual fee on both cards ($79 for the Plus, $99 for the premier). But hey, $180 for roundtrip airfare for your family is kinda a good deal. 
