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I wouldn't flag the post you linked to,... He's just bitching, I guess you are right that an honest discussion is better there :)

I have flagged very few posts, one example was a guy who kept on posting nude picture without using the nsfw tag

(It's okay to post nude pictures, but the nsfw tag is part of the community guidelines)

Also I would always recommend to comment the fact that you flagged, and to tell the person why...

That's my personal take on this issue, perhaps other people have other opinions on this...

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