Entering our 3rd year of SW CP
First two years were under me, next two under the SO. We use it religiously on a monthly basis to fly up and down CA to see the SO's family and friends up in the bay area.
Here are my tips on how to maximize free flights with SW:
1. Book in advance Flights are typically booked when there's a sale, and periodically checked and re-checked for any price adjustments. Since awards can be cancelled without penalty, its a no-brainer to book far in advance when there's a nice sale. Just make sure you don't book the companion until the last minute as it's much more difficult to get points credited back when a companion has been added.
2. Reduce your total travel cost. Outside of hotels and car rentals at your destination (if needed), there is the basic cost of getting to the airport. I live 15 minutes away from LAX, and ride my motorcycle to catch flights. Motorcycles park free in the central terminal, meaning no airport parking shuttle transfers. Just walk across the street and you're into the terminal. Having friends drop you off or taking public transportation also helps reduce this cost.
3. Credit cards can help you travel more efficiently, comfortably, and even cheaper. I have the Amex Plat card - annual fee is $450 but it comes with lounge access, plus $200 flight travel credit which I use each calendar year to buy $200 worth of southwest gift cards. These gift cards are then used in turn to pay for the $5.60 TSA fee for each award ticket. The Amex Plat also gave free global entry, which means free TSA Pre Check status that allows you to breeze by security lines, good for 5 years. There's the Citi Prestige that I'll be switching to avoid having to pay the Amex Plat annual fee again this year. It's $350 a year for the Prestige, but also comes with another global entry fee reimbursement (will use for MIL), lounge access, and $250 per calendar year flight credit (also to buy southwest giftcards), along with some nice sign up bonuses and other perks. Not having to deal with security at the airport, and hanging out in the lounge, and having the benefits of a premium credit card at basically no cost when you factor in the flight credits, is pretty nice.