Real-world examples of money-pumping?

In­tran­si­tive prefer­ences are a demon­stra­ble char­ac­ter­is­tic of hu­man be­havi­our. So why am I hav­ing such trou­ble com­ing up with real-world ex­am­ples of money-pump­ing?

“Be­cause I’m not smart or imag­i­na­tive enough” is a perfectly plau­si­ble an­swer, but I’ve been mul­ling this one over on-and-off for a few months now, and I haven’t come up with a sin­gle ex­am­ple that re­ally cap­tures what I con­sider to be the salient fea­tures of the sce­nario: a tan­gled hi­er­ar­chy of prefer­ences, and ex­ploita­tion of that tan­gled hi­er­ar­chy by an agent who cycli­cally trades the ob­jects in that hi­er­ar­chy, gen­er­at­ing trade sur­plus on each trans­ac­tion.

It’s pos­si­ble that I am in fact think­ing about money-pump­ing all wrong. All the nearly-but-not-quite ex­am­ples I came up with (amongst which were bank over­draft fees, Weight Watch­ers, and ex­ploita­tion of ad­dic­tion) had the char­ac­ter­is­tics of look­ing like swin­dles or the re­sult of per­sonal failings, but from the in­side, money-pump­ing must pre­sum­ably feel like a se­ries of grat­ify­ing trans­ac­tions. We would want any cases of money-pump­ing we were vuln­er­a­ble to.

At the mo­ment, I have the fol­low­ing hy­pothe­ses for the poverty of real-world money-pump­ing cases:

  1. Money-pump­ing is pro­hibitively difficult. The con­di­tions that need to be met are too spe­cific for an ex­ploita­tive agent to find and abuse.

  2. Money-pump­ing is pos­si­ble, but the gains on each trans­ac­tion are gen­er­ally so small as to not be worth it.

  3. Hu­mans have fac­ul­ties for iden­ti­fy­ing cer­tain classes of strat­egy that ex­ploit the limits of their ra­tio­nal­ity, and we tell any would-be money-pumper to piss right off, much like Pas­cal’s Mug­ger. It may be pos­si­ble to money-pump wasps or horses or some­thing.

  4. Hu­mans have some other ra­tio­nal­ity bound­ary that makes them too stupid to be money-pumped, to the same effect as #3.

  5. Money-pump­ing is preva­lent in re­al­ity, but is not ob­vi­ous be­cause money-pump­ing agents gen­er­ate their sur­plus in non-pe­cu­niary ab­stract forms, such as labour, time, af­fec­tion, at­ten­tion, sta­tus, etc.

  6. Money-pump­ing is preva­lent in re­al­ity, but obfus­cated by cog­ni­tive dis­so­nance. We ra­tio­nal­ise equiv­a­lent ob­jects in a tan­gled prefer­ence hi­er­ar­chy as be­ing differ­ent.

  7. Money-pump­ing is preva­lent in re­al­ity, but ob­scured by cog­ni­tive phe­nom­ena such as time-prefer­ence and dis­count­ing, or un­der­ly­ing hu­man aes­thetic/​moral tastes, (parochial equiv­a­lents of peb­ble-sort­ing), which hu­mans con­vince them­selves are Real Things that are Really Real, to the same effect as #6.

Does any­one have any­thing to add, or any good/​ar­guable cases of real-world money-pump­ing?