The rising frequency of natural disasters demands efficient and accurate structural damage assessments to ensure public safety and expedite recovery. Human error, inconsistent standards, and safety risks limit traditional visual inspections by engineers. Although UAVs and AI have advanced post-disaster assessments, they still lack the expert knowledge and decision-making judgment of human inspectors. This study explores how expertise shapes human–building interaction during disaster inspections by using eye tracking technology to capture the gaze patterns of expert and novice inspectors. A controlled, screen-based inspection method was employed to safely gather data, which was then used to train a machine learning model for saliency map prediction. The results highlight significant differences in visual attention between experts and novices, providing valuable insights for future inspection strategies and training novice inspectors. By integrating human expertise with automated systems, this research aims to improve the accuracy and reliability of post-disaster structural assessments, fostering more effective human–machine collaboration in disaster response efforts.