I've been teaching a one day seminar for 11 years- www.websitetology.com and the first problem isn't WordPress- it's that most people have no idea of how the web or search works. Without a basic understanding of what and how people search - and why wordpress works so well- you're kinda shooting blindfolded. The biggest challenge lately is trying to explain both the customizer and all these builders. The customizer is a disaster- a strapped on mess of a tool- that confuses more than it helps. The fact that a standard builder tool hasn't been adopted- makes things even harder. Widgets still confuse people- since they've been used to hack front pages for years. There is no shortage of info on the web on how to solve WordPress problems- I always tell my students- Google is your friend, but- because of all the new hack/non-standard ways to present info in a non-straight blog format- they don't even know what to search for. If they can just learn the importance of the taxonomy - posts, pages, categories and tags for organizing their info- they are ahead of the game- once they understand that pages and posts aren't the same thing- but are.... (yes- I just said that) the same in the end- they are in much better shape. All this being said- an integrated help system should be devised. Thanks for talking about this.