One thing that stands out in your steps and that I’ve noticed myself- yeah, by prompt 10, it starts to suck. If it ever hits “compaction” then that’s beyond the point of return.
I still find myself slipping into this trap sometimes because I’m just in the flow of getting good results (until it nosedives), but the better strategy is to do a small unit of work per session. It keeps the context small and that keeps the model smarter.
“Ralph” is one way to do this. (decent intro here: https://www.aihero.dev/getting-started-with-ralph)
Another way is “Write out what we did to PROGRESS.md” - then start new session - then “Read @PROGRESS.md and do X”
Just playing around with ways to split up the work into smaller tasks basically, and crucially, not doing all of those small tasks in one long chat.