Although I don't have a solution to your immediate requirement, I am working on a startup aimed at solving just this kind of problem. In other words, how to go from understanding the basics of a language to using it in an enterprise environment?
The idea is that a user uploads a real working application, then provides a series of guides through the different aspects of the project; configuration, security, mvc, testing, persistence etc
Unfortunately these examples use Java and Spring, but if by some miracle I can get someone to donate a ruby on rails example, you will be the first to know.
Integrating with version control systems, such as git, is quite high on my list of things to do (but it's a big list). My next move is to try and get other users to add their content onto the website, and github seems like an excellent place to start.
Also, you mention about proving that it is an efficient way to learn. That's a good point. Rather than assuming that people will like the format I should try to prove that it works, maybe by providing a comparison with some existing documentation.
Thanks for your reply kohanz. If you click on the underlined words in http://www.lishman.com/project/185#card/571/file/8007 a relevant section of the source code will be highlighted. I am looking to improve this with different types of highlighting in the future.
Example - http://lishman.io/angular-2-hello-world
Questions - https://goo.gl/IuLhhg