I'm new to WordPress and I'm trying to figure out a lot of things. I believe that you have great documentation, there are a lot of helpful docs that explain quiet everything. The problem is that they are not organized in the best way. I mean
Working with WordPress
they all say the same thing to me.
It's good that you give so detailing documentation but if don't organize it in a more user-friendly way, people can't easily find what the need.
Also in the Plugins Page, there is the same user-friendly problem. You should organize your plugins by category, not by tags, this is totally wrong. Take a look of Joomla way of organizing plugins. User just takes a look of categories and easily finds what he needs. Your search method also depends on tags and it returns too many irrelevant results. It's a matter of luck to find what you're looking for.
That's all I had to say. I hope this will be helpfull as an opinion to you.