A study was conducted to investigate the impacts of obstacles on pilot performance, workload, and perceptions of safety in a visual flight rule (VFR) obstacle-rich environment (ORE). The study was conducted using a piloted simulation of a single-rotor, multi-engine helicopter operating in a highly detailed urban visual scene database. The database contained multiple obstacle types, with variable obstacle heights and densities. Nine pilots completed the approaches and departures into and out of a heliport located in the center of the generic urban environment. Two flight routes offered unique presentations of terrain and obstacle types. Obstacle height/density and time of day/lighting parameters were systematically manipulated. A multi-dimensional data collection methodology employing the simultaneous collection of direct aircraft state, pilot performance data, pilot physiological data and pilot subjective responses was employed.This paper presents an overview of this experimental methodology, including data collection techniques. Problems and challenges encountered in designing and conducting this type of simulation experiment, as well as lessons learned from this activity, are also addressed. Specific data, results, or conclusions derived from this effort are not presented.