Image annotation is a time-consuming and costly task. Previously, we published MorphoCluster as a novel image annotation tool to address problems of conventional, classifier-based image annotation approaches: their limited efficiency, training set bias and lack of novelty detection. MorphoCluster uses clustering and similarity search to enable efficient, computer-assisted image annotation. In this work, we provide a deeper analysis of this approach. We simulate the actions of a MorphoCluster user to avoid extensive manual annotation runs. This simulation is used to test supervised, unsupervised and transfer representation learning approaches. Furthermore, shrunken -means and partially labeled -means, two new clustering algorithms that are tailored specifically for the MorphoCluster approach, are compared to the previously used HDBSCAN*. We find that labeled training data improve the image representations, that unsupervised learning beats transfer learning and that all three clustering algorithms are viable options, depending on whether completeness, efficiency or runtime is the priority. The simulation results support our earlier finding that MorphoCluster is very efficient and precise. Within the simulation, more than five objects per simulated click are being annotated with 95% precision.