An advantage of CAOS over traditional surgery is improved precision of implant position and trajectories in 3D space. However, the implementation of these trajectories often adds an extra step to the operation that increases operative time and requires extra training. This paper reports a study of variation in time-to-task and learning curve in performing a standard task of targeting in 3D space using Hull's CAOSS. It shows that time-to-task can be reduced by replacing a 3D targeting task with multiple independent 2D targeting tasks whilst potentially reducing targeting error. Based on this better understanding of targeting a novel jig was developed for performing dynamic hip Screw (DHS) insertion using CAOSS that would provide improved targeting performance by the surgeon.