Silat, do yourself a favor and don't compose any more stories. You have no concept of narrative flow.
That story ended, and its point was made, when the girl asked why the homeless guy doesn't earn his own money. Everything else was impotent wishy-washiness, searching yet never finding a conclusion as tight and complete as the one you'd already reached with the girl's honest, to-the-point question.
When she followed up with 'why doesn't he have a home?', a more honest answer would have been: 'because he's waiting for the democrats to build him one'.