Most of the examples I came up with, when I tried to formalise them, ended up being either rent-seeking or arbitrage.
My approach for finding money-pumping candidates seemed to be "in what ways are people scammed over and over again?" I've come to believe this approach is flawed, and my intuitions for what money-pumping would actually look like are off-base.
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:
Does anyone have anything to add, or any good/arguable cases of real-world money-pumping?