@dussla
I haven't done anything yet with AI (artificial intelligence) for CAD, but I think that your examples are too complex for PC... Some sort of manual drawing is necessary... All you could do is to try to divide area by some kind of grid - I used simple orthogonal scheme and still there may occur some errors... Still if I haven't already showed gif, I'll attach it here just for an info presentation...
Regards, M.R.