There are two sides to the coin with not being able to find things - sometimes it is, as you say, because you are bad at searching for things, but sometimes things haven't been made in an easily searchable way. To name just three: - sections with ambiguous names; - multiple sections with the same name; or - information is split across separate sections/pages.

Worst case is that there is detailed documentation but it's all in the comments of twenty different Jira tickets.

I do agree that user docs and dev docs should be separated though, as should specifications and development logs.