This paper investigates the application of high-resolution digital modeling through integrated 3D scanning workflows—Matterport for interior capture and drone-based photogrammetry for interior/exterior documentation—to support iterative planning strategies in the adaptive reuse of historic structures. While the use of 3D scanning technologies in heritage conservation is well established, this study contributes to the field by demonstrating how spatial, material, and infrastructural data derived from these scans can inform iterative design and technical integration strategies in architectural practice. Two case studies are presented to illustrate the workflow: the transformation of a 19th-century Baptist church into a performing arts theater, and the planned activation of a former photography studio and restaurant for contemporary art installations and design education. These sites serve as platforms for testing how digital modeling can support complex planning scenarios involving the retrofitting of lighting, mechanical systems, accessibility pathways, and exhibit infrastructure, all while maintaining the architectural integrity of the original structures. The resulting outputs—comprehensive, high-fidelity digital representations—are positioned as “digital models” rather than fully responsive digital twins, as they are not embedded with real-time sensor feedback. However, their utility extends across multiple phases of preservation and reuse, including stakeholder engagement through virtual walkthroughs, architectural coordination, and capital fundraising efforts. By centering digital workflows as a bridge between heritage documentation and future-oriented spatial interventions, this paper underscores the potential of 3D scanning technologies to enhance sustainability, accessibility, and design precision in adaptive reuse practices.