A few important points (pun intended).
* When you hit 110,000 miles/points (every dollar == a point), you get a free companion ticket ALL YEAR LONG that can be added at the very last minute. 50,000 is a very good start. But it gets better. Once you earn 110,000 points, you immediately get that free companion ticket this current calendar (2016) year PLUS the following (2017). I've hit free companion with ease every year (and my wife's card as well). Not through flying but though purchases. You can change your listed companion 2 or 3 times (I forget) per calendar year. You can use the companion ticket on a single leg of the trip.
* SWA doesn't have a minimum point schedule of 20,000 points like most reward cards/airlines. We have booked several tickets at 12,000 round trip from MPSP to DEN. It is extremely rare for us to use 20,000 points but we book early. Also, check back every-so-often if you paid a good deal of points. Points DO drop and you can re-book at lower points.
* MAJOR hint. ALWAYS book a single trip versus a round trip ticket. That way when your cadet's schedule changes, you re-book one leg and are not forced to drop them both.
* With a change or cancellation, SWA will give you back the small booking fee as well.
* Next key point: We always booked WITH MILES 2 trips from denver back home (our best guesses). Sometimes getting our cadet back to Denver has a last minute flexibility change too and you get another 6 hours before you have to report back. Hence we double book on the way home. When their schedule changes (and they will), you take the best flight of the bunch and cancel the others a week early. There is no penalty. But if you forget to cancel, that's a bad thing. Even small things change like your cadet validates a final and can leave 2 days early etc.
* SWA is very military friendly. At USAFA, they are considered Active Duty. We have gotten last minute tickets for cheap. They are not always available. But when they are, we have gotten an aggressive rate.
Yea, we are SWA bigots. We are HUGE fans. I don't work for them now am I a travel agent. We are just super delighted customers. For USAFA cadets, it doesn't get any better.