The chapter investigates an actionable model of virtual participation for learning communities, in the context of holistic student development in college education. The framework of analysis is based on scenario-planning, accommodating the dynamics of strategic design, decision making, and prototyping of various organizational scenarios of learning in communities. This conceptualization is extensible in cyberspace in today's World Wide Web, especially promising for today's universities, under the mission of ensuring quality student learning. The premise in this exploration is situated in the design of living and learning programs in residential colleges that must integrate the genuine concerns of holistic development for both teachers and students. What is often argued in this mesh of organizational design is how exactly to connect members of the communities, albeit the very behavior of hoarding personal presence (or knowledge) is what makes people feel secured and successful. The virtual participation model responds to this need by emphasizing the presence of an appreciative form of community sharing that could be facilitated through some innovative electronic channels designed into the daily living and learning experiences. However, the task of identifying what to watch for in building an online community of learning (CoL) is not at all straightforward. The authors' investigation provides a basis to think of the generative potential of appreciative processes for interaction among different CoLs. The emergent challenge is to de-marginalize the concept of appreciative sharing among CoL members, expositing on the effective meaning behind the creation of such an environment through which purposeful individual or organizational learning could be enabled with the elaboration of suitable information technologies. © 2012, IGI Global.