The basic idea here sounds great, but as someone who just went through a roughly similar training (self directed) over the past 4.5 months, I'd like to comment

The basic idea here sounds great, but as someone who just went through a roughly similar training (self directed) over the past 4.5 months, I'd like to comment on the choice for Python: I went through most of Learn Python the Hard Way: http://learnpythonthehardway.org/ http://learnpythonthehardway.org/ It was great! I then thought I'd do Codecademy for extra practice. It was so frustrating to use I gave up after a couple hours. Codecademy's automatic method for checking my code often indicated I had bad code without telling me why, when I had produced the correct answer. Furthermore, instructions were often unclear so I would often incorrectly interpret what the exercises wanted me to do.