For what it's worth, you can make the CSR free for the first year. If you book a Southwest refundable fare that costs more than $300, then cancel the fare after the credit posts, you can use that $300 for anything. You can also do that within the first 30 days of your second year holding the card, then cancel and get a full refund of the second annual fee. So, you actually come out +$50 and enjoyed all of the benefits of the card for a year. There are ways to repeat this process indefinitely, but that may be more complicated than you're looking for right now.
The point of me bringing this up is that high annual fee credit cards often have things like free night certificates, airline credits or other credits that make having the card a net positive, regardless of how you value the sign up bonus. Whether you keep the card long term or not usually depends on how easy it is to use those benefits. For instance, the Hilton Aspire card by Amex costs $450 per year, but has a free night at ANY Hilton (I often get $700-800 in value staying at a Waldorf or Conrad), plus $200 in airline credits I use every year and $250 in Hilton resort credits that I use at the aforementioned Waldorf/Conrad. So, I'm getting $1,000+ in value per year for a $450 annual fee (in addition to free Diamond status, which has lead to upgrades and other perks). This game is all about the big picture/long term value, but in some respect you're pre-paying for your discounted travel with those high annual fees.
