Habit tracking within Discourse...is it possible?

These look good, let me share some extra spice to your contribution @nolo.

I particularly like the Habit Tracker idea, it is something that has been done manually by Prof. BJ Fogg in his Tiny Habit Program. It really works and I use it in different areas of my life. I’ll suggest checking the program I linked to and checking the Discourse Policy plugin, you might see a possible hack to make it work in Discourse.

Then when you combine this with custom badges, I can see how it would be very sticky and habits will definitely build.

Taking this a bit further, while building on what I shared above and to help with the design part of your program @HedgeMage, may I suggest additional reading? The links I am sharing give an overview, but they will definitely help you better design habits.