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One thing that usually works well for questions that are answered in a guide/wiki/faq is to give a link directly to the section that answers it.
Users do tend to be very impatient and easily intimidated, so the smaller and more specific the section, the more likely people will read and use it.
They don't usually care about whys and wherefores (even though it's important to include in the documentation for those of us who do). They just want to know "how do I" for their specific need and to be given a 1.2.3. step-by-step answer.
Knowing what specific answer applies to their specific need is usually the hard part, and so there will always be repeat questions, but at least showing them a link to the answer is easier than typing out a full answer and explanation.
I need to go for a bit, but the other thing I'd suggest is labeling (even color-coding) things in terms of difficulty (basic/moderate/advanced), and letting it be known to users that more study effort is expected from them if they want to do things that require advanced understanding or experience.
A lot of us love to see calibre grow as a power tool, but the price of that is the effort it takes to keep non-power-users from being confused and power-users from being frustrated or overwhelmed with hand-holding them.
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