This chapter explores distinctions, opportunities, and critical issues in combining analog and digital techniques for creating hybrid representations of site designs at the scale of parkettes, plazas, and site details. The work featured showcases student work from studios and seminars taught by Maria Debije Counts and co-taught with Christopher Counts at the Pennsylvania State University. Initially, exploring design ideas through sketches is a loose way to begin the design process for small sites, but while drawings may inform or represent ideas about 3D space, there is a great disparity between 2D and 3D as a medium. Hybrid sketch models embody a three-dimensionality that 2D drawings inherently lack, such models are easily built up from sketch ideas that may be drawn in two dimensions. Hybrid techniques in analyzing existing site conditions such as annotated panoramic photographs taken on-site and site studies from digital geographic information systems (GIS) juxtaposes site experience with analysis and research.