I was the one who said it is about control.

He is placing all of these conditions on her, with the hope of a future, and that is control. What if she does get a license, car, and holds a job? He has no answer? The answer is that it will be something else next. He sounds like he needs to have all the control in a relationship. Do this, do that, don't do this. Isn't she old enough to decide these things for herself? Why is he trying to control her and tell her what to do?
A relationship is a two way street. What is this girl getting out of the relationship? It is clear what your male friend is getting out of it and what he wants to get out of it-- a second car, a second income, etc. What does she get? The privilege to be in his presence?
Anyhow, none of my questions are meant to be answered. You can open a million threads on this topic, and worry yourself sick about it, but the reality is that there is nothing you can do to change it. It's gone on for 2 years and will continue to go on until one of them decides to change it themselves. They are happy in their unhappiness for now. We all have different tolerance levels and breaking points. You have to just let this go for your own well being. Tell yourself that it is none of your concern.

If one of them comes to you and wants to complain about the other, just smile and tell them that it is not your problem and you would rather not hear about it.