In the domain of Advanced Air Mobility (AAM), Simplified Vehicle Operations (SVOs) promise a reduction in handling complexity and training time for pilots. Designing a usable human–machine interface (HMI) for pilots of SVO-enabled aircraft requires a deep understanding of task and user requirements. This paper describes the results of two user research methods to gather these requirements. First, a traditional Helicopter Emergency Medical Service (HEMS) mission was examined using a Hierarchical Task Analysis (HTA). The findings were used to formulate a theoretical HTA for a single-piloted electric Vertical Take-Off and Landing (eVTOL) system in such a scenario. In the second step, qualitative interviews with seven subject matter experts (pilots and paramedic support) in HEMS operations produced vital user requirements for HMI development. Key findings emphasize the necessity of a simplified information presentation and collision avoidance support in the HMI.