This week's events has led me to believe there's only one way to successfully run a community site: it must be owned by its users. As you already know, it's not easy to "monetize", especially without making the users mad. Reddit tried, with moderate success - the ads are unintrusive, and gold is OK, but this is still not enough. The community itself would be better off without these things. In addition, users of a community site will start to feel like it belongs to them, they are creating all the content, after all - so in a way it already is theirs. I don't have an answer for exactly how this would work out, but it would most likely look like a cooperative, as kleinbl00 writes. The more I think about it, the more I'm sure it's the future. I realize it would be difficult for you to give up something you own, and it could fail completely, but if it worked, then Hubski would grow to be something a lot larger and more important than it is now. It would take on a life on its own.