This chapter examines community empowerment, economic and business development, and equity of service as the issue of success and decline in regional and rural communities is explored with a particular focus on community informatics initiatives (CI). In Australia, there has been a vision for online services to be used to open up regional communities to the rest of the world. Government support has been seen as enhancing the competence levels of local communities so they become strong enough to deal equitably in an increasingly open marketplace. But how effective have regional portals and other online initiatives been? This chapter explores whether economic and social benefits are generated via establishing and sustaining regional CI initiatives. Theory relevant to online communities is introduced to provide a context for the presentation of two case studies. The dissemination of the critical learning from these cases can inform others about the diverse factors which impact on the effectiveness and long-term sustainability of regional CI initiatives.