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I want to be that guy that document everything, because I have seen the need for system to be completely documented. however, every time I start to document some system or code the info change or I'm away from it for a small while and the documentation and the system drifts apart.

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Exactly. Documentation is expensive and time consuming and needs to be maintained. They're absolutely great to have and can be vital, but it's up to management/leads to prioritize it because, at the end of the day, they decide where the money and man hours go.

This. Good documentation could easily take much more time than an actual implementation of a feature / system and what is an initial X days/weeks/months of estimation is not swallowed as easily by (some) management when you tell them it should be doubled if quality documentation is desired.

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