Abstract-Flight measurement is a critical phase in development, validation and certification processes of technologies destined for future civilian and military operational capabilities. This paper focuses on several recent NASA-sponsored remote observations that have provided unique engineering and scientific insights of reentry vehicle flight phenomenology and performance that could not necessarily be obtained with more traditional instrumentation methods such as onboard discrete surface sensors. The missions highlighted include multiple spatially-resolved infrared observations of the NASA Space Shuttle Orbiter during hypersonic reentry from 2009 to 2011, and emission spectroscopy of comparatively small-sized sample return capsules returning from exploration missions. Emphasis has been placed upon identifying the challenges associated with these remote sensing missions with focus on end-to-end aspects that include the initial science objective, selection of the appropriate imaging platform and instrumentation suite, target flight path analysis and acquisition strategy, pre-mission simulations to optimize sensor configuration, logistics and communications during the actual observation. Explored are collaborative opportunities and technology investments required to develop a next-generation quantitative imaging system (i.e., an intelligent sensor and platform) with greater capability, which could more affordably support cross cutting civilian and military flight test needs.