For flying all types of turbine-engine airplanes, a pilot must undergo an intense type rating (TR) course. This study investigated the learning conditions and TR course content, and specifies the most difficult course elements that could be tackled by augmented reality (AR) applications. Because women are underrepresented in the worldwide pilot population, it is important to address gender-specific preferences and needs in the development of AR-based wearable technologies for advanced pilot training. A gender-sensitive survey of the learning conditions and course contents was conducted with 31 pilots and 22 instructors. Despite many similarities, the results confirm that there are gender-specific needs and preferences for the development of future AR-based applications for TR training. In addition, the views of both pilots’ and instructors’ are required to obtain a comprehensive assessment of the learning contents and conditions related to TR. The results also show that time pressure increased the perceived difficulty of the course for some trainees. These results are important because they indicate the directions to be taken in developing future AR-based training applications for a more learner-centered and inclusive TR training. Future directions to foster a socially sustainable development of AR-based training means for TR with special focus on gender diversity are presented.