My gut feeling is that this worked better in the past because Stack Overflow was at a smaller scale, and the audience was a bit more insular and willing to read stuff about how the systems work on Stack Overflow (programmers love understanding rule systems; it's literally their job most of the time). Now that SO has achieved permanent world scale, the constant influx of new people who don't take the time to learn the ambient norms before posting, and thus cut themselves on what they perceive to be unnecessary sharp edges, is getting .. large.
Most of this could be solved by a very detailed, educational multi-step /ask page in my opinion.