Nice writeup! Been experimenting a lot with skills, agents and tools like GSD and honestly the biggest lesson for me has been: keep things short and simple.
Not just CLAUDE.md but everything, the prompts you type in a session, skill descriptions, agent configs, all of it. More instructions does not mean better results. Claude actually performs noticeably better with brief focused input. The moment you start over-specifying things quality drops.
Just my observation from using it daily but it's been consistent enough that I figured it's worth sharing.