Despite the success of Convolutional Neural Network-based Computer-Aided Diagnosis research, its clinical applications remain challenging. Accordingly, developing medical Artificial Intelligence (AI) fitting into a clinical environment requires identifying/bridging the gap between AI and Healthcare sides. Since the biggest problem in Medical Imaging lies in data paucity, confirming the clinical relevance for diagnosis of research-proven image augmentation techniques is essential. Therefore, we hold a clinically valuable AI-envisioning workshop among Japanese Medical Imaging experts, physicians, and generalists in Healthcare/Informatics. Then, a questionnaire survey for physicians evaluates our pathology-aware Generative Adversarial Network (GAN)-based image augmentation projects in terms of Data Augmentation and physician training. The workshop reveals the intrinsic gap between AI/Healthcare sides and solutions on Why (i.e., clinical significance/interpretation) and How (i.e., data acquisition, commercial deployment, and safety/feeling safe). This analysis confirms our pathology-aware GANs’ clinical relevance as a clinical decision support system and non-expert physician training tool. Our findings would play a key role in connecting inter-disciplinary research and clinical applications, not limited to the Japanese medical context and pathology-aware GANs.