[Feature Request] Implement 'Pain Mechanic' for Auto-Cleanup of Stale Project State

Feature Description
I'm watching this Cat Wu interview while I'm working and I thought I would make a request of something that is happening to me as I type this. I'm a veteran game systems designer, and I thought that it would be interesting to add a 'pain' system to trigger (similar to how the compact process is triggered automatically at a certain point) an update to the Claude.md file --- I'm not keeping track of it, and it has been a while... so sometimes I see Claude trying to reach for a file that no longer exists. So as a pain mechanic, you would just keep a counter in the back... of how many times Claude goes and tries to fetch something that is not there or something that is actually not as defined, let's say 36. so each time, it will +1 to this, once it hits 36, it would push a VERY strong recommendation to do either 'init' or a 'soft init' (so it is not super destructive and only focuses on fixing wrong stuff) --- I think that would be quite practical.

Environment Info

• Platform: darwin
• Terminal: vscode
• Version: 1.0.113
• Feedback ID: ce9bf290-de38-48a0-bf2f-a8ce24863108