While I take you at your word about the prep work you put in, in my experience, you're the exception rather than the rule. In general, when a new user doesn't understand how his article violates a policy, the sequence goes something like this:
User: "I don't understand what's wrong with my article!"
Sakaros: "Did you read the policy linked in the advisory template?"
U: "No."
S: "...read the policy linked in the advisory template."
U: (reads policy, fixes issue without further comment)
Some users do have follow-up questions, and of course Sebolto and I are always on hand to address and clarify any policy provision that isn't clear, but the flip side of that is that users have an obligation to educate themselves as much as possible. Since you mention Naming Conventions, that's one that commonly has violations that would leap out at anyone who read the policy (e.g. someone titles an article "Commander Example" instead of just "Example"). When it comes to the Spelling template, I've had a number of users who don't even read the entire template, let alone the policies (i.e. objecting that the article is American English, not British English, and ignoring the part about "spelling, grammar, punctuation, and word usage").
There are two templates that do often deserve a little elaboration: the above-mentioned Spelling and the Formatting template. Both embrace so many potential issues—and the Manual of Style is so long—that I try hard to give users direction in the Comments section of each template (e.g., for Formatting, "Page title should be bold in first use" or "Redundant categorization"). For Spelling, if there's a single consistent issue (e.g. failure to capitalize "Human") and nothing else, I'll drop a Comment about that, but if it's numerous and various spelling/grammar/syntax errors, I think it's an unreasonable expectation for an Admin to list every single one, particularly when MS Word has spelling/grammar check (and, I presume, the Mac version does too) and Grammarly and other sites will do online checks.
I've been doing this a very, very long time now, and I freely concede the policies are so intuitive for me at this point that they're all but baked into my DNA, which is not a reasonable standard for new users; that's why I'm always happy to clarify when someone comes to me with a detailed, "I read the policy but I still don't get what this section is saying" question. But when it's just "I don't get it", it's often a user who simply hasn't yet taken the time to put in the work, and while all users are entitled by the Editing Policy to bring a non-compliant article "up to code", at the end of the day, the author of a page bears ultimate responsibility for his creations.
All that being said, if anyone does have a specific example of a policy section or provision that's unclear or could benefit from elaboration or explanatory examples, I'm definitely willing to consider it.