The constant disappearance of hundreds of roshans, the projected wooden windows, in the historical city of Jeddah is now an established fact. Documentation is a major step towards heritage preservation, whether threatened by man-made or natural factors but no architectural database or measurement records exist due to the absence of specialists and experts. Thus, there is an immediate need for training new technicians and architects who could ensure documentation and conservation of remaining heritage. Thus, we propose a combination of new technologies, flexible, high interconnectivity, and high usability data formats to capture, model, and simulate these elements of heritage interest. For this purpose, an academic experiment involving architecture students from Jeddah was designed. The experiment required students to engage with a new integration of ICT-Hybrid technologies that incorporate dynamic and fast processes for 3D documentation and modeling. In this paper, we evaluate the usability of the proposed methodology as well as investigate ideas that may bring us closer to the goal of effective heritage documentation.