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OP, I am sorry that I cannot offer any immediate solution to your issue. However, if I may, pass along a bit of advice I learned long ago, and it has nothing to do with AI. TAKE PROLIFIC NOTES!!! It is tedious, it is work, but it will save your ass in the long run. Write everything down. Don't be lulled into the mindset that you will be able to remember each and every thing you've done to the server, especially when you're breaking new ground in your selfhosting journey. 9 times out of 10, you won't. Then when you are successful with your endeavors, go back, clean up your notes, and store them for future reference.
It doesn't really need to be tedious... My notes are jokey, full of profanity, sarcasm, and self deprecating humor
for context, these are my personal notes for my personal machine. These will never be shared with anyone else, and nobody else has to try to read them or make sense of them (well... sometimes I make chatbot read my notes in order to train it on whatever I need help troubleshooting)
Before I started keeping a hot_log.txt file every single install of Linux I ever ran was a unique snowflake and no two systems were ever the same
I meant tedious, as in, it takes some effort to pause, write the shit down, and then proceed on. I can only speak for myself, but when I'm in the zone doing something, excitement can overshadow note taking. So, I have to make myself document line by line. But, yeah I have entries like 'Before proceeding, make sure you do _____ , dumbass!' LOL
I very much wish I'd done this. I'm very happy with my system but it'll be a slog if and when I need to set it up again.