This is the first in a series of two letter reports detailing the specific test and evaluation requirements, scenarios, data processing techniques, and government/industry comments concerning pilot performance in an obstacle rich environment. The second report will develop and recommend the requirements for a piloted helicopter visual simulator to support data collection in this effort. This report details the issues and the development of test and evaluation criteria necessary to evaluate the psychological effects of an increasingly obstacle rich VFR heliport environment on the ability of a pilot to operate. In addition, it addresses a conceptual application of target level of safety, to assist the FAA and individuals concerned with heliport planning with regard to the proximity of obstacles to a VFR heliport. The effect of an increasingly obstacle rich helicopter environment on pilot performance will be tested by collecting definitive performance data through the use of a piloted, visual helicopter simulator. Results will be verified with actual flight testing. This study is divided into two phases. Phase 1 is further divided into four tasks: (1) test and evaluation requirements, (2) simulation requirements and facilities, (3) simulation test plan, and (4) pilot briefing materials. The product of task 3 is the completed test plan. The product of task 4 is pilot briefing material that explains their role in the test and participation requirements.