Helicopters are used in complex and harsh operational environments, such as search and rescue missions and firefighting, that require operating in ground proximity, tracking targets while avoiding impacting obstacles, namely a combination of point tracking (positive) and boundary avoidance (negative) objectives. A simulation task representing simplified helicopter dynamics is used to investigate point tracking and boundary avoidance tasks. The variance and regression analysis are used to study the effects of task conditions on participants’ tracking errors and input aggression. The overall tracking error shows a negative correlation with input aggression. The participants tend to have higher input aggression and lower tracking error near the boundaries, exposing the switching of manipulation input strategies under different task conditions. It also suggests a potential way of designing simulation tasks for human operators manipulating helicopters and a trigger for investigating pilots’ biodynamic feedthrough.