Although there has been great progress in robot grasp planning, automatically generated grasp sets using a quality metric are not as robust as human-generated grasp sets when applied to real problems. Most previous research on grasp quality metrics has focused on measuring the quality of established grasp contacts after grasping, but it is difficult to reproduce the same planned final grasp configuration with a real robot hand, which makes the quality evaluation less useful in practice. In this study, we focus more on the grasping process, which usually involves changes in contact and object location, and explore the efficacy of using dynamic simulation in estimating the likely success or failure of a grasp in the real environment. Among many factors that can possibly affect the result of grasping, we particularly investigated the effect of considering object dynamics and pose uncertainty on the performance in estimating the actual grasp success rates measured from experiments. We observed that considering both dynamics and uncertainty improved the performance significantly, and when applied to automatic grasp set generation, this method generated more stable and natural grasp sets compared with a commonly used method based on kinematic simulation and force-closure analysis.