I remember my first job as a intern at a company was to rewrite the documentation manual so I could "learn the system" While some things hadn't changed, the manual was 6 years old and there had been about 3 major releases that completely changed a lot of the UI. Also, all process documentation was out of date as new systems had come online and people had left. Now, this wasn't a commercial system that regular consumers would use, but I feel that sometimes I'm reading the manual and it seems like the people writing them have no experience with whatever it is and/or they're not technical enough to figure it out. The problem is that on one hand, you have engineers who would probably right a very detailed manual that people would get lost in or you have maybe the marketing people write it and it's missing important steps, etc. Hiring people JUST to do technical writing is an expense I don't think many companies want anymore so they hope to god it works otherwise you're stuck figuring it out or just buying another one.