Celebrating twenty-five years of acquiring, organizing and preserving grey literature in light of all the changes in publishing and information distribution gives us reason to highlight and parse communication technologies and methods. The organizational structure, emphasis on visualization and data, new applications of artificial intelligence, instant communication, and the convergence of technique with practice offers a lens in which to assess how social media has evolved. This suggests how opinions from certain sources matter as does the reshaping of consumer preferences that often dictate unexpected outcomes. Applications for business transactions, crowdsourcing, social learning, community building and flash mobs each attract different populations motivated by a range of goals. Matching these goals with appropriate social media conduits is the focus our work. Social media today has demonstrated that eMail has given way to shorter and faster methods of communication such as text-messaging, tweeting and using any number of mobile apps to distill and manage one’s inbox. The changes in communication strategies indicate that the level of expectations is reduced and challenges the retention of these transcripts for future needs. Generational differences and practices are studied by social and information scientists interested in the implication of how data elements in social media have proliferated and beg the question of whether they need to be managed, archived and preserved by whom and for how long. We also explore the changing values of social media. In this milieu of data reuse and repurposing, the multiple channels of social media are challenged to determine maximum efficiencies for alternative solutions in business and daily life. The unintended consequences of social media misuse are increasingly concerning in the wake of false reporting leading to fake news in our perceptions of creating a more evidencebased and transparent society. Whether social media drives marketing or vice versa is ultimately what determines the prominence of greyness remains central to these queries. Methods of engagement and interaction vary depending on the form of social media and the capacity to channel different data points such as images and photos, opinions, preferences, promoting a brand or selfanalysis. This paper explores how “the reach” to target audiences has become central to the goals of accomplishing business and social transactions and what the implications are for long term learning, commerce and communication effectiveness, a sustained reliance on social media and what the significance is for retaining trusted content in a variety of environments that currently emphasize living in the moment.