Thank you for the compliments, but wisdom was acquired at the price of decades of mistakes. I am not so sure if I was lucky or unlucky the cool jobs fell into my lap but I didn't sweat and take advantage of them. And so I had up and down cycles that rival the best roller coaster.
Steven, I think you have nothing to lose by asking. But isn't this the type of career where you need education? Isn't the cheap labor the grad students? I think there is nothing wrong with asking but expecting a scholar to teach without the student willing to take the courses is something he should be prepared to address. If he can get into the university and then approach, it would probably leverage his opportunities immensely.
I never go on a job interview without being prepared, I know what the company does, I know what I do, how I can do what they don't have. This Robert Bakker has a bunch of enthusiastic grad students that are really jumping all over themselves to work with him. And they have to as part of their school work and they are probably free. I think approaching Robert Bakker is fine, but applying to the school may be a first step.
Ren