More tips:
1. If the fare drops after you buy, you can easily change it online to the lower fare. Even though you go thru the motions like you're changing flights, you can still choose the same flight again at the lower fare. You then keep the credit which you have 1 yr from original purchase date to use. There is no fee for doing this. For one person it's not a lot but for a family it can add up. We ended up with a $300 when our Thanksgiving fares dropped.
If you want to change to a Ding fare, you have to cancel the original, not just change it, and apply those funds to the Ding flight. The phone reps are very kind and will walk you through it.
2. Book as separate one way flights. It's usually the same price and this makes it easier to change/rebook if the fare drops.
3. When searching for fares for more than 1 person, I still enter 1 passenger. Let's say you're searching for 4 people to Orlando. Also let's say there's 3 seats available at $59 one way. If I enter 4, it may bump up the price of all 4 seats to $89. If I start searching for 1 then 2 then 3 people, I learn that I can buy 3 seats at $59 then only have to pay $89 for one rather than all 4. Does this make sense?
4. Have him check in online at exactly 24 hrs. before his flight. SWA boards in numerical order of when each person checked in. (Except those that need extra assistance and families with children under 4.) Each boarding pass is assigned a letter & number like A20 or B18. First those needing assistance board (wheelchairs, etc.) then the A's board 1-45, then families with kids under 4, then B's 1-45, then C's. (I'm pretty sure A's and B's only go up to 45. Can someone help me out here?)
5. I like SWA that you can check 2 bags pp with no fees, no seating or change fees and their schedule rarely changes except when due to weather or mechanical issues. For us it's only been related to weather. They still serve free soda and crackers/nuts.
6. There are no inflight movies but can bring his own entertainment (dvd player, iPod, etc.)
hth