There has been a bit of recent discussion on comments and anonymity on the web. See Anil, Tim, Caterina, and Anil again. Good stuff for the most part, but I have a bit to add from my perspective.
For several years, I ran a site called Anonyblog. I've taken it down now, so there's not much to see now. You could probably Google it or find it on archive.org if you are really interested.
The premise was simple. I made a weblog and posted the username and password to allow anyone an anonymous way to post on a weblog and "get it off their chests". I was enthusiastic about blogging at the time, fresh from inspiring SxSW conferences and watching traditional media adapt to the influence of bloggers.
My plan was simple, let people post whatever they wanted, stand back and let the good times roll. I was quite naive.
At first, things went as I intended. Posts on all types of issues from work, relationships, politics, police departments, other bloggers, and even requests for advice. Occasionally there were posted that I found distasteful, but in the name of 'freedom' I didn't censor anything.
At one point someone starting posting NSFW photos. Being that I was checking on the blog from home, I didn't want my children seeing NSFW photos while I requested that people not post NSFW photos. This was the first rule I made.
Things were OK for a bit more, and then a group of posters appeared that appeared to already know each other. They posted inane stories about stuffed animals and racist stuff, and appeared to encourage each other in this. I really didn't like it and considered deleting it all, but ended up leaving it alone. "It's just words." I said to myself.
Fairly quickly a contingent of readers started pushing back and complaining about the stories. The frustration on both sides escalated and soon I was dealing with users deleting and revising the posts of others. Some users were even posting fake posts from their 'enemies' to make them look bad.
Suddenly, I was in moderation overdrive trying to maintain some sense of order. It was a pain for me, but I did it because occasionally someone would post something that I felt worthy or that gave someone that was hurting a way to relive their pain.
I worked on ways to auto-approve posts to prevent editing by others and free me from having to individually approve each post. I spent many hours trying to solve the now communities' problems.
The group of stuffed animal story people soon invited yet another friend to post. This person was obsessed with coprophagy (Google it yourself, I won't link it). Multiple posts, images, and all sorts of disgusting stuff way over my personal limits for freedom. I pushed back hard, deleting stuff and banning IP addresses.
Soon I was in a war with the shit poster. He would use scripts to auto-post hundreds of posts via proxies. I would script deletions, use anti-spam software to filter words he used frequently, and even started tracking down the person via IP in an attempt to dox him.
I posted to the community about the issues so people knew what was going on. A few cheered, but many harangued me over my censorship. WTF? I'm the guy who built the Anonyblog in the beginning and did a bunch of work to keep it running. How dare they question me?
At this point, I knew the end was near. I started to feel anger and hate toward users. At some point, the blog software broke due to either the external attacks or my defense modifications. No new posts were possible at this point.
I could have fixed it, but I didn't.
Why? Well, people could still post in the comments, so they did. And it just got worse. Terrible stuff, fighting, and everything bad that occurs in online communities when the brakes are removed.
For a couple years, I agonized over what to do. I talked to a few people I respected as having wisdom in blogging community expectations. More than once I was ready to relaunch the site, but just couldn't since I knew it would bring ever more drama and frustration into my life. I felt bad, since I knew there were many people out there suffering that could use an outlet for their pain.
In the end, I wiped the site clean. The web is a better place without it.
What did I learn? Two things really.
First, people do need anonymity. There is pain, secrets, desires, worries, successes, failures, and prayers that people have and need to share in a way that they feel safe. Going to an all 'Real Name' internet does not help many people.
Second, complete anonymity and anarchy leads to the worst in people. Even a tiny group can poison a community, creating divisiveness and bad feelings all the way round. Without fail, this is what I saw on Anonyblog and in other communities on the web when anonymity reigned.
To make Anonyblog work would require many of the things Anil mentions in his post. I just don't have the time, energy, of desire to build all that to support what would be needed to prevent a site like Anonyblog from becoming a sewer once again. But the need for it remains.