This would be my number one request. I'm great in my field, but I didn't go to school for anything computer related. Nevertheless I designed my own first website from scratch (pre XHTML, PHP etc.); taught myself two languages (ancient dialects); learned government code in a month when I needed it, etc. Yet I can't get my plugins to work! I have done a lot of reading on the forums, on the documentation, and other areas; yet the documentation assumes a lot of knowledge that endusers who are not IT people just don't have. And I have much more than most people I know.
Do this, and you'll see a sharp increase in users. Just because a person isn't tech-savy, doesn't mean they necessarily should be over on wordpress.com, because they may have a business they need to use the software for.