The case experience of anesthesiologists is one of the leading causes of accidental dural punctures and failed epidurals - the most common complications of epidural analgesia used for pain relief during delivery. We designed a bimanual haptic simulator to train anesthesiologists and optimize epidural analgesia skill acquisition. We present an assessment study conducted with 22 anesthesiologists of different competency levels from several Israeli hospitals. Our simulator emulates the forces applied to the epidural (Touhy) needle, held by one hand, and those applied to the Loss of Resistance (LOR) syringe, held by the other one. The resistance is calculated based on a model of the epidural region layers parameterized by the weight of the patient. We measured the movements of both haptic devices and quantified the results' rate (success, failed epidurals, and dural punctures), insertion strategies, and the participants' answers to questionnaires about their perception of the simulation realism. We demonstrated good construct validity by showing that the simulator can distinguish between real-life novices and experts. Face and content validity were examined by studying users' impressions regarding the simulator's realism and fulfillment of purpose. We found differences in strategies between different level anesthesiologists, and suggest trainee-based instruction in advanced training stages.