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I'm not who you asked, but i do the same thing, i keep important state in doc files and recreate sessions from that state. this allows me to clear context and reconstruct my status on that item. I have a skill that manages this

Using documents for state helps so much with adding guardrails.

I do wish that ChatGPT had a toggle next to each project file instead of having to delete and reupload to toggle or create separate projects for various combinations of files.

This is why claude code/codex cli is the way to go for me because often they can recompute the state from the minimal description automatically. If i relaly do needto stop the session and come back in i can point it at the task file. it also has docs and scaladocs/javadocs in key places. good naming and project structure helps it very easily find the data it needs without me needing to feed it specific files. I did the 'feed it files and copy paste the code snippet' thing in chatgpt for months. wish i went to claude code sooner.

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