Isn't this a grand country, the good ol' USA?
If you speak Spanish, wade across the Rio Grande, you have five free passes and only get done by the law on your sixth illegal ingress to the country. If you overstay a visa you get may get nicked, but immediately get turned loose to await your court hearing and you can skip out on that with no great chance of being "pursued". Unless such a person gets arrested for a crime, there is scant risk of his being chased down and then be deported.
Here we have a young lad that wants to work, pay taxes, and assimilate the culture while providing a Professional service using abilities gained at his own expense here in the USA, but there is no way for him to obtain a Work Visa because the good ol' American government does not consider him to be a "Professional" because the immigration folks say flying licenses do not equate to a University Degree therefore helicopter pilots are not qualified "Professionals".
That to me, is a rotten way of doing business.
I wonder if one applied for an extension to the current visa or for a new visa saying he was continuing his "education" by enrolling at a community college and obtaining another "student visa" for that purpose.....would not that allow one to "work" while attending that course of education? Could that be stretched out for a four year period.