I like the content, but I wish it was a blog so that I could simply follow the RSS feed.

Literally, your ideas are intriguing to me and I wish to subscribe to your newsletter.

Someone with spare time should be able to write a quick CI script to build a blog with any static site generator.

The structure is perfect for that, of course. :)

You could grab https://github.com/thoughtbot/til/commits/master.atom and select commits beginning with "TIL *" with Yahoo Pipes or something similar. I agree though, other posters' suggestions of gh-pages would be nice.

Here's an RSS feed: https://github.com/thoughtbot/til/commits/master.atom

With github pages isn't that just a few setup steps away?

I keep my notes in an emacs .org mode document. I suspect a lot of people do this kind self improvement.

Why don't just make a single README.md and then split it if grows enormous.

A wiki might be helpful.