I've recently received a substantial amount of feedback about the Debian Community Guidelines and went into some reorganization of it.
The previous general section still stands as the Main Guidelines: those are the substantial few things to always keep in mind.
What previously was the long list of checklists is now split in two: the Debian-specific Guidelines, which should be a shorter lists of non-obvious suggestions for people who already have experience with online life, and the General Guidelines, with the fuller checklists with useful suggestions for everyone.
I still haven't gone through the selection and reorganization of the Debian-specific and General part, so at the moment they look fairly similar and most things overlap. But the good news is that I finally found a structure that I like, and that can allow more experienced people to make use of the guidelines without getting bored with simpler things like "google before asking a question".
This division also suggests a little workflow: new suggestions can be added to the Debian-specific part, and then later moved to the general part when they become obvious for everyone.