For us, it has definitely been worth it. Last year, I applied for the signature Visa and the business Visa, both at 50,000 bonus points. This gave me the companion pass for last year and this year. Recently, I applied for the standard card, with the 50,000 point offer. Once I get 14,000 more points, I will have a companion pass for next year also. We use the card for pretty much all purchases and pay off the balance every month. We also take advantage of e-rewards and the shopping portal on the SW site, making it easy to get more points. Since last year, we have flown 5 of us to Orlando RT, 3 of us to DC RT, 2 of us to Orlando RT, 4 of us to Ft. Lauderdale RT, and one person to Chicago RT. I still have well over 100,000 points. As far as the $99 fee, you do receive 6,000 points on your anniversary so it's pretty much a wash.