In this presentation, we report on a spectrum of investigations that explore the influence of observations and observational strategies. First, evaluations of the assimilation of high-resolution satellite datasets in the mesoscale WRF and COAMPS-TC models as part of the National Oceanographic Partnership Program will be highlighted. These findings will be complemented by recent evaluations of the influence of in-situ observations from manned and unmanned aircraft, and supplementary rawinsonde data. Observing strategies and data impact methods will be summarized. Finally, Observing System Simulation Experiments that consider configurations of future observational platforms will be introduced. The presentation will conclude with a summary of strengths and weaknesses of the various methods and strategies employed, and recommendations for the coordination of future studies with multiple new observational datasets.