We live in an era in which the ways that we can make sense of our past are evolving as more artifacts from that past become digital. At the same time, the responsibilities of traditional gatekeepers who have negotiated the ethics of historical data collection and use, such as librarians and archivists, are increasingly being sidelined by the system builders who decide whether and how to provide access to historical digital collections, often without sufficient reflection on the ethical issues at hand. It is our aim to better prepare system builders to grapple with these issues. This paper focuses discussions around one such digital collection from the dawn of the web, asking what sorts of analyses can and should be conducted on archival copies of the GeoCities web hosting platform that dates to 1994.