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One thing that would help me out would be if new documentation could point out which parts of a system are needlessly complicated and which parts are needed for the system to function. If a book or document could just say "This part of the tool is waaaay too complicated because the original developers envisioned this evolving differently. These are the good parts that you should spend time learning". I think Douglas Crockford called this "subsetting". A big challenge when approaching a new technology is deciding which parts to invest in.

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