In 2016, with the support of a three-year National Endowment for the Humanities (NEH) Collaborative Research Grant to research and write a precolonial African history of family, generations, and gender, we began building the Bantu Ancestral Roots Database (BARD). BARD is a digital repository of word-roots related to gender and life stage practices from over sixty Bantu languages. We developed it to assist us in our analysis of this large corpus of data that we used to write histories of people’s material and ideological inventions that cover the longue durée across multiple regions. BARD allows researchers with internet access to search for terms by entering at least three consecutive phonemes. If phonemes exist in that sequence in any of the 64 Bantu languages that BARD holds, those words and their meanings appear as results. In this article, we discuss the usefulness and complexities of Digital Humanities (DH) as research tools. We explain our methodology and research process using three reconstructed word-roots pertinent to our research on family and generations. The three word-roots we examine invite scholars to probe how to recover deep connections and linkages between people’s pasts in Africa and its Diasporas, particularly in ways that move beyond histories of the slave trade and enslavement. As we developed our open-access website African Social History and Data Across Bantu Matrilineal Communities (ASH-DABMC) and our database, BARD, we gained greater insight into the meanings encoded in our data even as we faced challenges. We hope the discussion of our experiences will provide an intellectual framework and inspire others considering digital projects.