We consider the field of machine learning and where it is both useful, and not useful, for the distribution grid and buildings interface. While analytics, in general, is a growing field of interest, and often seen as the golden goose in the burgeoning distribution grid industry, its application is often limited by communications infrastructure, or lack of a focused technical application. Overall, the linkage of analytics to purposeful application in the grid space has been limited. In this paper we consider the field of machine learning as a subset of analytical techniques, and discuss its ability and limitations to enable the future distribution grid. To that end, we also consider the potential for mixing distributed and centralized analytics and the pros and cons of these approaches. There is an exponentially expanding volume of measured data being generated on the distribution grid, which, with appropriate application of analytics, may be transformed into intelligible, actionable information that can be provided to the right actors - such as grid and building operators, at the appropriate time to enhance grid or building resilience, efficiency, and operations against various metrics or goals - such as total carbon reduction or other economic benefit to customers. While some basic analysis into these data streams can provide a wealth of information, computational and human boundaries on performing the analysis are becoming significant, with more data and multi-objective concerns. Efficient applications of analysis and the machine learning field are being considered in the loop. This paper describes benefits and limits of present machine-learning applications for use on the grid and presents a series of case studies that illustrate the potential benefits of developing advanced local multi-variate analytics machine-learning-based applications.