Is it a 1:1 ratio for points? If so, then you need the full $20k by the end of the year, so I could see how that could be difficult. It’s a Chase card, right (sorry for my ignorance, we just never fly Southwest, so I’m not as familiar with the card as some others) If so, what about a shopping portal to get extra points? Or is it just straight amount of money?
Depending on how close you are, and exactly how much you would save on a companion pass for the year, you could always look into a service that will let you pay your rent/mortgage with your credit card for a 2-2.5% fee. Normally I would never do this, but if you have multiple flights next year that would only require you to pay for one ticket, that extra service fee *may* be worth it.
I’d give you some of my travel, but then I may lose the opportunity for two free tickets to Australia


It’s a tough decision- go with the sure thing or roll the dice and hope for the bigger reward. I have to say that it is a fun game though. I’ve gotten some pretty great redemptions on previous flights. Not nearly to the level that some people have, but I still feel pretty good about them.