Thanks a lot for your help everyone.
So I've managed to get something that kind of works using the the Formulas and MathyThing plugins (thank you to whoever made them!). I've attached it here.
Currently you just tag a tiddler "habit" and it appears on the list. Clicking a button adds an entry in a data tiddler as "yes" or "no".
The code is a total horror show (tons of copy + paste...), but I'm interested interested in constructive criticism on the basic idea. Specifically how the data is stored. I feel that as long as I get that right I can fiddle with everything else in the future when I'm better at using TW.
I would also like to calculate the "percentage success rate" for a given week, so if anyone has any advice on how I could do that it would be super appreciated? In other words I want to look at only the data entries for the last seven days and calculate what percentage of them were set to "yes".