The process of architectural design aims at solving complex problems that have loosely defined formulations, no explicit basis for terminating the problem-solving activity, and where no ideal solution can be achieved. This means that design problems, as wicked problems, sit in a space between incompleteness and precision. Applying digital tools in general and artificial intelligence in particular to design problems will then mediate solution spaces between incompleteness and precision. In this paper, we present a study where we employed machine learning algorithms to generate conceptual architectural forms for site-specific regulations. We created an annotated dataset of single-family homes and used it to train a 3D Generative Adversarial Network that generated annotated point clouds complying with site constraints. Then, we presented the framework to 23 practitioners of architecture in an attempt to understand whether this framework could be a useful tool for early-stage design. We make a three-fold contribution: First, we share an annotated dataset of architecturally relevant 3D point clouds of single-family homes. Next, we present and share the code for a framework and the results from training the 3D generative neural network. Finally, we discuss machine learning and creative work, including how practitioners feel about the emergence of these tools as mediators between incompleteness and precision in architectural design.