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.