Very well written article. I think everyone can definitely emphasize with the confusion that comes with having to dig through APIs and tooling for the first time.

When a friend asked me to teach him some python the most stressful part for him was setting up the editor, understanding the command line and how an API worked as well. Like the author he grasped fundamental python pretty quickly.

I think there's still no really good solution to make the whole process appealing. You can have people write puzzle solutions which circumvents the API and documentation issue but doesn't produce a real project, you can give them an IDE which avoids the command line but doesn't teach much and often is too complicated for a simple script, and so on but there's always some nasty issue for beginners in the process.