Flagging, to me, seems like pissing in the wind. If I notice serial posters submitting extremely low effort content (a pair of their own posts every waking hour from "6 months and 5 minutes ago", off-topic wikipedia nearly once a day, "I have 60000+ points but only upload from thealtantic/guardian/nytimes") then I go on an irate ten-minute flagging binge.
I've also been aghast at the nerve of those same serial posters applying the letter of the law against other users. I genuinely wouldn't care if Bartosz Ciechanowski only self-promotes every last one of his own posts. Some users are significantly more interesting than others, whether or not they violate the site guidelines marginally on a technicality.
I have suspected it's possible some users flags are worth more than others, and I wouldn't be surprised if my flagging ability was silently removed several years ago.