Skeletal spatial structure (SkS) systems are modular systems which have shown promise to support mass customization, and sustainability in construction. SkS have been used extensively in the reconstruction efforts since World War II, particularly to build geometrically flexible and free-form structures. By employing advanced digital engineering and construction practices, the existing SkS designs may be repurposed to generate new optimal designs that satisfy current construction demands of contemporary societies. To this end, this study investigated the application of point cloud processing using the Field Information Modeling (FIM) framework for the digital documentation and generative redesign of existing SkS systems. Three new algorithms were proposed to (i) expand FIM to include generative decision-support; (ii) generate as-built building information modeling (BIM) for SkS; and (iii) modularize SkS designs with repeating patterns for optimal production and supply chain management. These algorithms incorporated a host of new AI-inspired methods, including support vector machine (SVM) for decision support; Bayesian optimization for neighborhood definition; Bayesian Gaussian mixture clustering for modularization; and Monte Carlo stochastic multi-criteria decision making (MCDM) for selection of the top Pareto front solutions obtained by the non-dominant sorting Genetic Algorithm (NSGA II). The algorithms were tested and validated on four real-world point cloud datasets to solve two generative modeling problems, namely, engineering design optimization and facility location optimization. It was observed that the proposed Bayesian neighborhood definition outperformed particle swarm and uniform sampling by 34% and 27%, respectively. The proposed SVM-based linear feature detection outperformed k-means and spectral clustering by 56% and 9%, respectively. Finally, the NSGA II algorithm combined with the stochastic MCDM produced diverse “top four” solutions based on project-specific criteria. The results indicate promise for future utilization of the framework to produce training datasets for generative adversarial networks that generate new designs based only on stakeholder requirements.