I think much of Reddit's problems with its userbase boil down to an early failure to manage expectations. It's pretty clear that the Reddit corporation doesn't want Reddit to be an anything-goes, absolute free speech zone with no moderation or anti-harassment policies -- but that's what the site actually was for many years. Now, when the company cracks down, users think their freedoms are being curtailed. The mistake…
Removed some words to make this statement more accurate.
Reddit itself doesn't manage the communities, and that's a problem because the Thought Police are now doing it for them.
The idea that people should be allowed to create and manage their own communities is nice in theory, but why should Xx_JoeSchmoe123_xX be in control of the largest League of Legends community? Just because he hit the 'Create Subreddit' button before anyone else? That makes no sense, but it's how all of Reddit is run.
Reddit probably thinks "This is great! We've got all these community managers (moderators) working for us and we don't even have to pay them!" But the quality of their moderation is often proportionate to their salary...