For example, this person[0] could have simply booked a United flight from the United site for 15k points. Instead the person batch emailed Turkish Airlines booking offices, found the Thai office that was willing to make that booking but required bank transfers in Thai baht to pay taxes, made two more phone calls to Turkish Airlines to pay taxes with a credit card, and in the end only spent 7.5k points for the same trip on United.

This may be an extreme example, but it shows the amount of familiarity with the points system, the customer service phone tree and the actual rules to get cheap flights.

[0]: https://frequentmiler.com/yes-you-can-still-book-united-flig...

This sounds interesting?

Just don't book a round trip, don't check a bag, don't do it too often. Also you're gambling that they don't cancel your flight and book you on a new one to the city you don't actually want to go to (that no longer connects via the hidden city). You can get half price tickets sometimes with this trick.

https://www.bitsaboutmoney.com/archive/seeing-like-a-bank/

> As a sophisticated user of the banking system, a useful skill to have is understanding whether the ultimate solution to an issue facing you is probably available to Tier Two or probably only available to a professional earning six figures a year. You can then route your queries to the bank to get in front of the appropriate person with the minimal amount of effort expended on making this happen.

> You might think bank would hate this, and aggressively direct people who discover side channels to Use The 1-800 Number That Is What It Is For. For better or worse, the side channels are not an accident. They are extremely intentionally designed. Accessing them often requires performance of being a professional-managerial class member or otherwise knowing some financial industry shibboleths. This is not accidental; that greatly cuts down on “misuse” of the side channels by that guy.

Persistent mispricings can only exist if the cost of exploitation removes the benefit or constrains the population.

But if you wanna find the cheapest way to get to A, compare different retailers, check multiple peoples availability, calculate effects of credit cards etc. It takes time. Aren't those things that could be automated with an agent that can find the cheapest flights, propose dates for it, check availability etc with multiple people via a messing app, calculate which credit card to use, etc?

An LLM could organise flights with a lower error rate, however, when it goes wrong what is the recourse? I imagine it's anger and a self-promise never to use AI for this again.

*If you're saying that the AI just supplies suggestions then maybe it's useful. Though wouldn't people still be double checking everything anyway? Not sure how much effort this actually saves?

When I'm picking out a flight I'm looking at, among other things:

* Is the itinerary aggravatingly early or late

* Is the layover aggravatingly short or long

* Is the layover in an airport that sucks

* Is the flight on a carrier that sucks

* What does it cost

If you asked me to encode ahead of time the relative value of each of these dimensions I'd never be able to do it. Heck, the relative value to me isn't even constant over time. But show me five options and I can easily select between them. A clear case where search is more convenient than some agent doing it for me.

It's the same problem with Alexa. I don't trust it to blindly reorder me basic stuff when I have to shift through so many bad product listing on the Amazon marketplace.

With a really excellent human assistant who deeply understood my brain (at least the travel related parts of it), it was kind of nice. But even then there were times when I thought it would be easier and better to just do it myself. Maybe it's a failure of imagination, but I find it very hard to see the path from today's technology to an AI agent that I would trust enough to hand it off, and that would save enough time and hassle that I wouldn't prefer to just do it myself.

Because there is no "correct" flight. Your preference changes as you discover information about what's available at a given time and price.

The helpful AI assistant would present you with options, you'd choose what you prefer, it would refine the options, and so on, until you make your final selection. There would be no communication lag as there would be with a human assistant. That sounds very doable to me.

In one chapter he describes his frustration with GPS based navigation apps. I thought it was similar to what you describe.

> If I am commuting home, I may prefer a slower route that avoids traffic jams. (Humans, unlike GPS devices, would rather keep moving slowly than get stuck in stop-start traffic.) GPS devices also have no notion of trade-offs, in particular relating to optimising ‘average, expected journey time’ and minimising ‘variance’ – the difference between the best and the worst journey time for a given route.

For instance, whenever I drive to the airport, I often ignore my GPS. This is because what I need when I’m catching a flight is not the fastest average journey, but the one with the lowest variance in journey time – the one with the ‘least-bad worst-case scenario’. The satnav always recommends that I travel there by motorway, whereas I mostly use the back roads.