The contribution concerns the development of methods and protocols for the monitoring of historical built Cultural Heritage with an integrated multidisciplinary approach consisting of documentation activities and analysis procedures. In particular, the latter concern the state of the art, morphology, construction technologies, and the conservation state of materials and construction packages, to structure the corpus of knowledge of the asset under examination. The analysis procedures aim to understand the spatial components of the structure in relation to construction, technological, and material aspects, and to define the digitization actions to be activated on the artifact based on the observed condition. Understanding and monitoring of the cultural asset is achieved through the construction of synthesis frameworks, functional for describing its complexity, which culminate in the use of semi-automated and automated censusing systems of Information Systems for the formulation of monitoring protocols and programmatic frameworks for management. The methodology for automating the monitoring and the architectural census using Object Detection algorithms on georeferenced orthoimages is tested on the follow-up of the AICS co-funded cooperation and research project “Management and control of urban growth for the development of Heritage and improvement of life in the city of Bethlehem” (3D Bethlehem), in which the University of Pavia had scientific responsibility and the research laboratories STEP and PLAY of the Department of Civil Engineering and Architecture were involved.