A system for the augmented assessment of digital media streams for virtual less than insertion opportunities is disclosed. A digital media stream is automatically decomposed, using a programmed digital processor, into one or more candidate-clips have a predetermined minimum length, and no internal shot transitions. These candidate-clips are then examined, and the ones deemed suitable for virtual insertion use, are classified as viable-clips and stored in a digital database. The artificial intelligence techniques of machine learning and deep learning are then used to further classify the viable-clips according to their virtual insertion related attributes that may be attractive to advertisers, such as scene context, emotional tone and contained characters. A value is then assigned to the viable-clips, dependent on their insertion related attributes, and the overlap of those attributes with client requested requirements.