At this point I'm fully down the path of the agent just maintaining his own tools. I have a browser skill that continues to evolve as I use it. Beats every alternative I have tried so far.
Plus, now it is personal software... just keep asking it to improve the skill based on you usage. Bake in domain knowledge or business logic or whatever you want.
I'm using this for e2e testing and debugging Obsidian plugins and it is starting to understand Obsidian inside and out.
I can try to write it up (I am a bit behind this week though...), but I basically opened claude code and said "write a new skill that uses the chrome debug protocol to drive end to end tests in Obsidian" and then whenever it had problems I said "fix the skill to look up the element at the x,y coordinate before clicking" or whatever.
Skills are just markdown files, sometimes accompanied by scripts, so they work really naturally with Obsidian.
https://notes.danielgk.com/Obsidian/Obsidian+E2E+testing+Cla...
Your skill will be tuned to your use case over time, so if there's something that you do a lot you can hide most of the back-and-forth behind the python script / cli tool.
You can even improve the skill by saying "I want to be more token efficient, please review our chat logs for usage of our skill and factor out common operations into new functions".
If anything context waste/rot comes from documentation of features that other people need but you don't. The skill should be a sharp knife, not a multi-tool.