Reading list from Philip Guo’s Human-Centered Programming Tools class at UCSD http://pgbovine.net/human-centered-programming-tools.htm

If anyone's looking for quick, live, visceral ways of 'feeling the pain of the user' for programming languages, his pythontutor site has an anonymous chat-based live help feature. You can just hop on and help someone with their coding, and connect to real frustrations and confusions (and help someone out!) http://pythontutor.com/visualize.html#mode=edit

Some pretty good stuff there man. MIT CSAIL group mentioned there has produced some pretty cool stuff in this niche.