but still driving them away because what seemed like constructive argument from one side didn't from the other.
Or still driving them away because the comment stream petered out before people got around to expressing their changed viewpoint and the contrarian left because he never realized he was having an impact. The post and comment format isn't really very good for a serious back-and-forth discussion. Especially when posts are so briefly on the front page, note that this is another good reason for getting meet-up announcements OFF of the discussion page.
I'm worried that LW doesn't have enough good contrarians and skeptics, people who disagree with us or like to find fault in every idea they see, but do so in a way that is often right and can change our minds when they are. I fear that when contrarians/skeptics join us but aren't "good enough", we tend to drive them away instead of improving them.
For example, I know a couple of people who occasionally had interesting ideas that were contrary to the local LW consensus, but were (or appeared to be) too confident in their ideas, both good and bad. Both people ended up being repeatedly downvoted and left our community a few months after they arrived. This must have happened more often than I have noticed (partly evidenced by the large number of comments/posts now marked as written by [deleted], sometimes with whole threads written entirely by deleted accounts). I feel that this is a waste that we should try to prevent (or at least think about how we might). So here are some ideas: