[MidlifeFlyer]

I told you you piqued my curiosity. I still have some touble with the concept, given all the "grey charter" cases that go into a "holding out" analysis - why bother if it makes no difference whether they were holding out or not?

But, in addiiton to your 1988 Opinion, I found one from 1992 (I don't know what the reg said at the time) involving a company that sells vehicles. It plans to rent an airplane from a flight school (we're obviously not talking about Part 125 aircraft) to transport its own employees to pick up the cars. In the course of saying it's okay, the Opinion goes on,

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I would caution you against allowing this arrangement to evolve into a de facto operation of private carriage for hire. This would occur if you, in fact, put together the transportation package consisting of aircraft and pilot services and received payment for the operation of the flights, even if the clientele was limited to one customer. This would require a commercial operator certificate.
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I'm not completely satisfied for my own purposes yet, but thanks for bringing this to my attention.