The original poster isn't doing any of those things, or at least, didn't mention it. What does it matter what he's doing? 135? Spraying crops? Towing banners? Instructing? Playing freight dog? Taking pictures from the air? Dropping jumpers? Flying around in his own airplane?

What's the difference, if he flies his own airplane around and logs it, or someone pays him and he logs it? Would there be a difference if he did X (insert your own special kind of flying, as apparently you don't like the example of ag or back country flying) flying, if he got paid, vs. simply did the flying himself? Pick a kind of flying. He pays. An employer pays. The flying doesn't change. The location doesn't change. The weather doesn't change. He doesn't change. The only difference is who pays...does one make him a lesser human, and the other, an exalted being? Hardly.

Why does it trouble you, so?

When he arrives at his first job, will they care?

He will show up a minimally-qualified applicant with the hours necessary to apply, and that's all they'll really care about. They'll train him from there. Just like everybody else.