Originally Posted by Yoshamano

If you don't mind snagging a couple of gift cards and "buying" some points, hang on to the card. Buy a $75 Southwest gift card https://www.southwest.com/gift-card/home.html to use your $75 travel credit (that's what I did to use my credit). So you end the year at -$74 of value. Next year you renew the card so you're at -$223. However, you get 7,500 anniversary points. For the sake of argument lets say they're worth $0.01/point. So now you're at -$148. The part you'll need to fill in is how many upgraded boardings you're buying. For this lets just assume it's you, and I'm assuming it's a middle of the road upgrade so $30. Now we're at -$118. It's a new year though and you have another $75 credit so buy another gift card if you can't spend it on a flight.

So we finally end up at -$43.

If you need 3 upgrades instead of just the 1 then you end up in the black $17. The 2x points on Southwest purchases and 20% in-flight purchases are small peanuts (especially with no beverage service), but still might account for something.

Play with the numbers and see where they land for you. Then decide if you should cancel or not.