Supporting expert communities is becoming a 'must-have' capability whenever users are helping each other solve problems. Examples of these expert communities abound in the form of enthusiast communities, both inside and outside of organizations. In order to achieve success, these systems have to connect several different actors. In this paper we aim to inform the design of these Hybrid Intelligence Systems through the investigation of StackOverflow. Our focus in this paper is to develop indicators for hard problems and experts. The long-term goal of our study is to examine how complex problems are handled and dispatched across multiple experts. We outline implications for modeling these attributes and how they might inform better design in the future.