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One thing I do in my workflow is to create a dedicated page for my stylesheet. As I'm working, I often times will need a new class on the fly – and since I'm a lazy mofo – I don't go to my stylesheet page and style the element there, I make it wherever I am and keep working. Which means a few of my classes don't make it into my stylesheet.
Now, I know the answer could just be, "Just be more disciplined, a-hole!". BUT, iff there was a 'send style to stylesheet' button where I could create a styled element on whatever page I'm working on, and then have the style auto-copied to my stylesheet page... well, that would be amazing.
Haha! Love your description. I think something like this could be solved with a dedicated style guide page. We're thinking about this too!