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"Craigslist inverts this relationship and puts the power into the readers' hand"No, it doesn't - it puts powers into other advertisers' hands as much as it does the users. You are also forgetting that time is not a fundamentally equal resource - in my case it seems like there are griefers on the subcategory who consistent (and around the clock, it seems) flag posts that rub them the wrong way. Perhaps it's other regular posters trying to push competing posts out of the way (very, very likely, and in fact a common tactic), or maybe a disgruntled user with a beef against a subcategory and too much time on his hands. The problem here is griefers - and there is no mechanism to stop them.
Compare this with MMORPGs - players with a lot of time on their hands can stand to be incredibly powerful in ways that normal players cannot. Most games balance for this by nerfing extreme regulars and boosting infrequent players to lessen the gap. It doesn't remove the incentive of playing more, but it prevents situations where a bunch of Lv. 100 wizards are just constantly destroying a bunch of Lv. 10 noobs. CL faces the same problem - the morality police, griefers, and other obsessive users gum up the entire system.
> "That so many here are angry about having gotten flagged off in the past tells me that they were doing the bare minimum in writing their ad anyway."
This is an attitude I saw a lot on the flag-help forum, but I read through a large number of threads and I'd wager 95% of them were just fine - neither violating the TOU, nor being offensive, nor being illegal... There are many lower-traffic subcategories where the flag threshold for being pulled is absurdly low.
That's the problem with flag-help. Most posts submitted there don't have anything obviously wrong with them, and the flag-helpers are either there to flog the newbie for daring to have a post that got flagged, or speculate on various non-obvious reasons why a post was flagged. In the end nobody gets anywhere except in the 5% of cases where the questionable nature of the post is obvious, this is pointed out, and everyone goes on their merry ways.
> "By and large the people most frustrated with their Craigslist posting experience are those who just barf out a self-serving ad and expect the invisible hand of Adam Smith to protect their "right" to get $1200 for a Britney Spears ticket."
Citation required. I hung out on the flag-help forum for a couple of hours after posting my own, digging through past posts. The vast majority of the posts that go through there are neither self-serving nor entitled. They're just normal ads that get pulled for seemingly inexplicable reasons. The flag feature is neither accountable nor does it come with context. All there is is speculation on maybe, kind of, probably why something was flagged, where really this information needs to come from the flaggers themselves. The usage of the flag as an offensive feature between posters is also almost trivially easy to stop, but yet CL has done nothing.
The flag-help forum posters are also ill-qualified for the job, since they don't have any data on why posts get flagged either! All they can do is speculate - but without any input from real flaggers their speculation is about as reliable as anyone else's. For obvious offensiveness this works, but from what I saw the vast majority of posts that pass through there were flagged for anything but obvious reasons, and the responses are not informed.
> "If this was your experience, I'd look to the attitude of the person asking for help."
I gather from the tone of this sentence that you're a flag-help poster yourself. I saw dozens of puzzled people come into the forum, be perfectly respectful and polite, only to be faced with snark and derision from the "old boys club" of flag-help users. The prevailing attitude was "how dare you post something that got flagged, you sketchy sleazebag you! Here's some random speculation from me because there's nothing obviously wrong with your post, and your confusion and bewilderment as a result will only be further proof that you are not only posting shite content to the site, but clueless to boot!"
I've given up on Craigslist entirely from both a user and advertiser perspective. Mass-posters routinely flout the minimum-post-frequency guidelines, with nobody seemingly policing this abuse. Large advertisers will routinely flag competing posts to weed out competition. Griefers make the smaller, low-traffic subcategories impossible to use. Craigslist used to be a reliable way to just find simple classifieds, but the griefers and spammers have gotten more savvy and are exploiting the system straight to hell, and CL is still operating in the bubble of "the users know what's best" when their main audience has little to no say at all.