Army Aviation is evolving from over a decade of training aircrews with aircraft using analog systems to an era of digitization, simulation, and embedded processing. Training Centers are adapting to this changing environment characterized by a common operating environment by reusing hardware and software across platforms. This evolving environment not only enhances individual aircrew skill levels, but collective air to ground integrated (AGI) operations training. The Army’s Aviation Tactical Engagement Simulation System (Aviation TESS) is capable of conducting individual, crew, and collective training to facilitate unified land and air operations training at the Combat Training Centers (CTCs) and Home Stations. Aviation TESS material developers must plan for life-cycle upgrades to adapt and integrate new technology, new tactics, techniques, and procedures (TTPs), and new training venues. Aviation TESS is currently used to collect aviation data across existing Army Aviation platforms (Apache, Black Hawk, Kiowa, and Chinook) and, in the future, from the ground component of the Unmanned Aircraft Systems (UAS). This paper provides information on current aviation training capabilities, challenges faced by live aviation training stakeholders, and how PM TRADE will use the principles of Better Buying Power to evolve training systems to meet long-term Army aviation training requirements.