This user was not attempting to ask bad questions or question on how to exploit or get around the system. He was asking questions about understanding how to negotiate some difficult situations. I see no reason for the excessive down voting of the duplicates. That they are duplicates not bad questions. It is a testimony to the way the system works that we already have answers to many of this users questions. But I do not see anywhere that was a serious attempt to explain to the user how to use the system to find the answers, or to explain to the user why their other questions were being closed or how to ask better questions.
This has resulted in a user that appears to have abandoned SE all together. One thing that stands out to me is that most of the comments, lacking any ability for use to read actual emotions, could easily be taken as dismissive, uncaring, and snobby. We missed the mark on the "Be Nice Policy" with this user at every turn.
So what can we do to improve here? Is there some way we can make the site more friendly to new users?