This is an interesting idea! In the alternate playground [1], the frontend is React / Redux and so we already track every edit to the code as well as the build results. "All" that would be needed would to save that data somewhere and allow people to opt-in/out.
I think that a quick survey of the user would be helpful as well- specifically their experience with programming, and their experience with the language in question.
[1]: http://play.integer32.com/