This paper discusses how live linkages between parametric geometry, structural analysis and optimization can be leveraged to explore an architectural massing from different perspectives of optimum assuming a set of cost and value characteristics. Broad performance measures such as program area, cladding surface and structural quantities were computed for each geometry variation and collected. Optimums from different perspectives (structure, developer, designer) were extracted for each height category and compared. To further inform and engage stakeholders, a variety of visualization and filtering techniques have been implemented. These new techniques and associated distillation of data aids the design team in understanding the design space. A script based approach towards geometry and data management has led to a shift towards active option evaluation and a more interactive approach to form exploration. A generic workflow for structural analysis, design and optimization has been implemented and this ability to engineer at a greater velocity will move the design profession towards a more collaborative and information based design environment.