This chapter investigates design strategies for developing digital musical instruments (DMIs) for participatory music. In particular, we present strategies to enhance collaborative musical skills such as rhythmic entrainment and listening/responding to other participants: building skills of this kind has the capacity to motivate long-term usage and adoption of the DMI by a broad range of communities. The design strategies described here address the problems of developing DMIs for long-term use, both in collaborative, mixed skill level contexts, and in established musical and dance traditions. Interactive Tango Milonga—presented here as a case study—is an interactive dance system allowing social tango dancers to drive musical outcomes in real-time via their dance movement. Motion sensors are attached to dancers, and the signals from these sensors are sent to a computer, where an algorithm transforms them into tango music. The impact of the interactive tango system on the musical listening and response of tango dancer participants is analyzed and discussed.