Segment run?
 

I didn't travel much this year due to a new baby, but I'll be back in the saddle next year. I did 41 segments in 2018, but only 14 this year. So, I can add two LAS segments to 2 upcoming trips, then do 4 PHX-LAS runs (the last one including an LAX pop-in for that final segment) to make A-List. Cost around $520. Would you do it?

I was on the fence, but I just got home ~5 hours earlier due to same-day standby. I jumped to the head of a 9-person standby list and saved $280, both thanks to A-List.

I know this is subjective, but I'd love your thoughts.

Just to be clear, WN doesn't actually count "segments". They count one-way trips as a single "flight" (which may include multiple segments) for A-List qualification. Are you sure each of these segments will count as a separate "flight"?

The trips will count if booked on separate PNRs at each stop.

The "Getaway Fare Finder" was great for putting back-to-back cheap segments together, but now it takes more work finding these combinations.

$520 for A-list? That depends on how much you plan to fly Southwest in 2020.

I've booked a couple of flights extra, usually an optional trip, to get A-List in the past, but I doubt I'd spend $520. If I was that short I'd probably just pay for Early Bird. $520 would buy 20-30 early birds (assuming they don't raise the price again), almost enough flights to qualify for A-List. You wouldn't get the Bonus points so that could be factored in.

If the work schedule you'll be returning to next year will allow you to take advantage of the standby perk fairly regularly, I'd go for it. That is a fantastic benefit. While I can't actually value it at face value - I wouldn't usually pay the fare difference to fly earlier - I do value it highly. Add in autocheckin, A61 boarding, and a few extra points, and I wouldn't have much trouble rationalizing it away. Check recent threads, someone put something really impressive together recently...

:D (... and it wasn't that bad, actually)

Nice! If I had had more foresight I would have done that run with you!

I'd spend that $520 next year to either get A-List sooner and/or do a mix of EB and Upgraded Boarding purchases. Maybe 8 $39 legs, 6 EB at $15, and a couple of UBs.