Why does Greg hate flying Southwest? | Ask Us Anything Ep 59


This past Wednesday we had another fun evening answering questions from readers. For instance we had a surprisingly hard time narrowing down the options for a reader who asked which credit cards make the most sense for international economy flights (27:33 ), and Greg spilled the beans on why he doesn’t like flying Southwest (25:54).

Watch the full episode above, or click the timestamps below to navigate directly to a specific question within YouTube.

00:00 – Start

03:34 – Hey Nick, now that you’ve traveled on a few “free” cruises, what info did you learn along the journey that you wish you had known about from the very beginning?

06:10 – Greg how is the buyers group experiment going?

11:05 – I wanted to offer a counterpoint to your recent Southwest CPP post with the companion pass. How can IHG points ever be worth more than 0.5 cpp? Let’s say you redeemed 100,000 IHG points for a hotel stay that was priced at $2,000 (or 2cpp per usual calculations). However, those 100,000 points can be bought easily for $500 many months out of the year. shouldn’t you only say that you got 0.5 cpp out of that because anyone could have bought 100,000 points for $500, and subsequently redeemed it for our $2,000 hotel?

18:15 – How do you utilize local banks and credit unions in this hobby if at all?

21:23 – How many times can I upgrade a Freedom card to a Sapphire Card and downgrade again before Chase gets upset?

23:14 – Best Maldives property. Hyatt or Hilton Conrad or Hilton WA or something else?

25:54 – Why does Greg dislike Southwest so much?

27:33 – What is the best airline credit card for international economy class travelers?

35:02 – Would you sign up for a new card if you were going to be financing a car in the next month or so?

36:18 – Thoughts on LH biz (747-400 upper deck, for what it’s worth)? I grabbed an award because it was the exact date I needed. Not exactly excited about it, but I’ll never complain about business class.

37:43 – Best hotel co-branded card – Hilton Aspire or Ritz Carlton?

41:35 – How does the 1.54 Cents Per Point AMEX BIZ PLAT cash back trick work?

43:17 – Based on your article about Bonvoy signup bonuses, it seems to suggest that if you currently hold a Ritz Carlton card you cannot get the signup bonus for the Bevy card. Did I interpret this right?

44:13 – How do we get free nights at Fairmont Properties in Canada? I know they shut down the credit card years ago, but is Fairmont similar to Four Seasons where there isn’t a way to redeem points?

49:40 – Looking to start earning Wyndham points, for Vacasa…. what’s a better path? Citi or CapOne?

52:32 – Getting started on American miles. What would your credit card strategy be?

53:30 – Is it worth mattress running 11 cat1 nights at a local Hyatt (38,500 pts) for guaranteed suites for 2 wks in HKG? I’ve never had or used any SUAs. Thx!

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Also I think Greg is based out of Detroit, which really doesn’t make sense for Southwest (as opposed to SkyTeam/Delta)


I agree with Greg on SWA. It is a simple fact that for humans, uncertainty causes stress. Not knowing where you will sit, worrying about the mad rush to crowd the gate to get a good seat, worrying about if your group can find seats together, that uncertainty creates stress. Do some people actually like that, or do they just tolerate it? I really don’t get it. For me I would never fly SWA unless it is literally the only option…and even then I’d probably take the option of just not going. I hate SWA boarding process that much.


I don’t think anyone really likes the flying process for Southwest, but they do have some good things going for them. They are typically the cheapest and have great availability in my area (I live in the Southwest US), they offer 2 free checked bags, Companion Pass is great, and no change or cancellation fees (although most other airlines have matched this since COVID).

The actual flying experience is pretty subpar, but if the flight is only for a few hours its not too bad. For me, all these things make SW a contender in my book, even with all the downsides you mentioned. Think of them like a Pseudo-budget carrier, somewhere between Frontier/Spirit and the Big 3 airlines.


This might be too industry-gooberish for points enthusiasts to care about, but their irksome processes are more apparent ever since they made moves in the Gary Kelly era to be a full-fledged national carrier, compared to Herb’s model of being everything/nothing to different market segments.

When their bread and butter was banging back and forth within/between Texas, Vegas, Phoenix, and California 1,000 times a day, it didn’t matter. The person connecting across the country was an afterthought and they were on the record saying as much. Show up at DAL or SAN or ONT as close to departure as possible, sit down, and be there. Even on the runs where a legacy went head to head, there was no more joy to be had flying America West or some Skywest CRJ-200.

It’s a tougher sell however (to me at least) when I’m going 3/4 of the way across the country, and their competitive set is broad.

The unfortunate bit is that their “big airline” model also diminishes the quality of the classic milk runs. Those are now enmeshed into the larger network, so performance issues ripple to them as well. That’s a problem because on those runs they’re basically public transit and often somewhat fungible with driving.

I secretly wish they would somehow isolate the shuttle runs because they’re really two opposing network planning goals. Do old-fashioned sit-down-shut-up Herb service on them, that’s fine, but keep them reliable. They’re unlikely to do this, however, as the side of the road is littered with failed airline-within-an-airline attempts (Shuttle by United, Delta Shuttle, Ted, Song, etc.).


Southwest has been love it or hate it since they began. I think if I lived in a “normal” market I would have a different take on them, where comparisons with other airlines are more straightforward, but the California air market is a really unique animal, particularly if you bounce up and down the state a lot.

Despite having multiple large-hub airports, Intra-California flying is utterly dominated by Southwest, and they guard this market jealously. In the early 90s, with PSA vacated, they quickly realized their “Texas triangle“ model of 1-hour flights that 1) are somewhat fungible with driving and 2) demand robust frequency applied well in this state.

Further, the prevalence of side airports really means you’re not even necessarily doing LAX-SFO (where there is admittedly more competition), but just as likely to be doing something like BUR-OAK, to say nothing of the other medium-sized cities in the state like San Diego, OC metro, IE, or Sacramento each maintaining robust north-south connections.

Basically, if you’re up and down the state a lot it’s a rare person that doesn’t just tuck themselves in with Southwest and let that be that.