Expert beginners? You mean humans trying to answer poorly worded questions?

Learning new things can be hard from some people, but generalizations that all of any type of software is hard make me sad. That being said, I've switched people from wordpress to Drupal, mostly by asking them what they want to do in the future, then showing them how it eventually is the road to having to pay for features. That is usually enough to convince them that Drupal is the right choice or a custom solution is better.