Cool idea and sounds like a fun project! However, Github pages has supported HTTPS for a while [1]. Personally, I like free over a cup of coffee any day.
When people try to migrate their shell scripts to a friendlier scripting language I'm always reminded of this post about "Bruby"[1]. It's a compelling argument to move to something comfortable but it also means you're at risk of just using Python's easy "if" and string-parsing logic when you're still relying on shell script tools for the core functionality.
Using a directory watcher to rerun ruby unit tests on file changes was something that helped me do more TDD. Having a terminal open and seeing it turn from red to green as tests start to pass on every save is a very satisfying feeling. Saving and manually re-running your tests after changing what should make the next test pass is not.
What's interesting is these aren't the same posts that are at the top of hot for /r/the_donald.
Archive link for when this is fixed by reddit: http://archive.is/4nJCw
[1] https://github.blog/2018-05-01-github-pages-custom-domains-h...