re: What is a free man?
You have to be careful on this. Metaphysical "freedom," such as freedom from hunger or freedom from pain is not the same thing as political freedom. Confusing these two is a common tool of those who aren't in favor of political freedom.
In my experience, someone who tries to stretch the definition of political freedom and its foundation in individual rights into a long and complex series of analyses is probably trying to pull a fast one somewhere.
Most of the big questions in the world have relatively simple answers. If you keep hearing answers to these questions that are complicated and incomprehensible, it's usually because the simple answers aren't the answers people want to hear.