This paper presents data related to helicopter sling load stabilization and MEDEVAC (Medical Evacuation) rescues collected by cadets performing research in the field at the United States Military Academy (West Point, NY) and Sapienza University of Rome (Rome, Italy) since 2018. The aim of this paper is to identify engineering constraints in MEDEVAC rescues. Constraints in two typical scenarios are presented. This information can then be included in simulations and models of swing stabilization and hoist control methods. Information is obtained through a literature review and interviews with U.S. Army helicopter pilots and crew chiefs who perform MEDEVAC rescues.