Not what you're looking for, but:
I didn't know him very well personally, but there was somebody in my circle of acquaintances who I heard was in the habit of doing things like buying a new gaming console and then realizing that he didn't have the money to pay his rent because of that. Then he'd sell it to someone for substantially less than the original price, so that he'd get at least some money quickly. Then he'd repeat essentially the same process a few months later.
Apparently his "friends" liked him because they'd get cheap stuff from him. I imagine that he would have been very easy to provoke into buying something (and thus selling it off later), but if anybody I knew was doing that intentionally, they never admitted it to me.
From your description, he sounds merely bad at budgeting.
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?