This could be as simple as extending the "If you're new here" message a bit to be a group of bolded links at the top of each page pointing to the Guide, FAQ, How To, and Tutorials.   The links could persist until the fresh Monk advanced to Novice(2) or Acolyte(3).

Question for our fearless leader and crew: Is this reasonably do-able within the Everything engine?

You can't force folks to read before asking, but if the FAQs and such were more prominant for visitors and new Monks, the Monastery should stand a better chance at continuing to be the almost-always friendly place we all enjoy.
    cheers,
    ybiC