Probably not in the core plugin but I do think a "help plugin" would be valuable. One idea which has been discussed is to turn the docs into a plugin. And one could imagine a "beginners edition" where this was included. However, I think the current administrative infrastructure hinders such ideas because it would put too much administrative burden on Jeremy.
IMO to solve this we'd really need a totally different infrastructure. I mean, even the docs are not enough - as clearly evidenced by this very board. I think TWederation is the only way we could solve this in a realistic way. It would allow us to build a federated knowledge base kind of like interacting wikipedias or StackOverflows everywhere. Easier said that done - but Jed has taken the first steps with me cheering in the background. I hope to pick up on it pretty soon again. (must just finish this other suuuper cool TW thing or three that I'm working on...)
<:-)