But drawing from imagination is just copying from an abstraction existing in your brain. And that abstraction comes from inputs from the outside that you saw in the past, where would it come from if not that?

In the Obama example it comes from copyrighted inputs. Without the photos in the magazines and newspapers I would not have idea how Obama looks. Any draw I do, it's going to be derivative of those copyrighted photos and, maybe, other inputs more generics that I saw in the past (that could be copyrighted too).

How is that different from what that software is doing? It's not, it's just that it's done in an industrial scale.

This is just the same problem an artisan had when factories started to appear.