Families use a range of devices and locations to capture, manage, and share digital photos as part of their digital photo ecosystem. The act of moving media between devices and locations is not always simple though and can easily become time consuming. We conducted interviews and design sessions in order to better understand the movement of media in digital photo ecosystems and investigate ways to improve it. Our results show that users must manage multiple entry points into their ecosystem, avoid segmentation in their collections, and explicitly select and move photos between desired devices and locations. Through design sessions, we present and evaluate design ideas to overcome these challenges that utilize multipurpose devices, always-accessible photo collections, and sharing from any device. These show how automation can be combined with recommendation and user interaction to improve flow within digital photo ecosystems.