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But if your docs really are a bottomless pit, it might behoove you to invest in your community instead of documentation. Grow some in-house experts and put them on the forums and a chat system. Send your users there instead of to increasingly out-of-date help docs and get them in the habit of searching for answers there. Build a reputation for responsiveness to get free customer loyalty on the side. Send your UX people and engineers to the forums as well so they get the pulse of your most frustrated customers. Slowly your community will become your experts as well.
There's a training side to education and there's a wisdom side to education, and they're both important in the long run. Telling young people to get jobs right out of high school because being well-rounded isn't necessary for "smart" people just means it's going to be a crap shoot as to whether their decisions repeat history or learn from it.
Well, it just happened.
I don't think we disagree on any specific points so far. I'm not trying to replace security audits, just to encourage people who do the right thing without being paid to do so.