Over the past number of years, I've put in a lot of time developing and maintaining resources that are open (in varying degrees) to the world. While I do consider these projects more than worthwhile, sometimes they can be hard to deal with. While there are always problems-- with time, financially, or with other resources-- it seems that the biggest headaches always come from within. In this talk, we'll look at a few communities of varying degrees of stability I've been involved with, the problems that have come up in and because of these communities, and the steps taken to help solve these problems. These will include things created both online (2600net, aculei.net) and in the real world (the Hacker Halfway House, the current yet-unnamed project I'm working on).