Clover Kicker (probably not his real name) has written an amusing article on Kuro5hin.com (“technology and culture, from the trenches”). Although officially a guide for writing “bad documentation,” it’s really a guide about what differentiates good documentation from bad documentation.
Probably the most important lessons here is that more documentation isn’t necessarily better documentation, and the more documentation you have, the harder it is to maintain.
Of course, the lessons here are true of any document that needs to be kept up-to-date over time.
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