Background: Can we create a technological solution to flexibly self-manage undergraduate General Surgery practices within hospitals? Before the pandemic, the management of clerkships was starting to depend less on checkerboards. This study aims to explore undergraduates’ perceptions of doing rotations in teaching hospitals using different teaching styles and elicit their views regarding the options of managing practices to design a mobile app that substitutes for checkerboards. Methods: In this sequential exploratory mixed methods study, 38 semi-structured interviews at a teaching hospital were conducted. The data was used to survey 124 students doing their rotations in four teaching hospitals during the first wave of COVID-19. Results: 21 themes highlighted concerns related to the practices, the teacher involvement in the students’ education, and the students’ adaptation to clinical culture. The students reported positive perceptions concerning self-managing and organizing practices via a mobile application. However, problems emerged regarding transparency, the lack of feedback, and the need for new tools. Regarding the teaching styles, the facilitator and personal models were perceived as optimal, but the personal style had no effect on using or not using a tool. Conclusions: A mobile-learning application designed like an educational opportunities’ manager tool can probably promote self-directed learning, flexible teaching, and bidirectional assessments. However, teachers who employ a personal teaching style may not need either checkerboards or a tool. This solution supports teaching at hospitals in pandemic times without checkerboards.