Documentary Relations of the Southwest (DRSW) is a dataset of bibliographic metadata derived from over 1500 reels of microfilmed documents that trace the history of the southwest from the 16th century until Mexico's independence in 1821. Originally made available to scholars through a now defunct proprietary repository, DRSW’s future is currently being assessed in the context of other repository solutions. While migrating content is a familiar scenario, this migration highlights key challenges in navigating the intersection of legacy design and possible futures for metadata curation and repository selection. This presentation deals with challenges revolving around three paradigms: metadata as content, system documentation generation, and metadata futures for indexing and integration