We have implemented a system to automatically analyze Chandra x-ray observations of point sources for use in monitoring telescope parameters such as point spread function, spectral resolution, and pointing accuracy, as well as for use in scientific studies. The Chandra archive currently contains at least 50 observations of star cluster-like objects, yielding 5,000+ sources of all spectral types well-suited for cataloging. The system incorporates off-the-shelf tools to perform the steps from source detection to temporal and spectral analyses. Our software contribution comes from wrapper scripts to autonomously run each step in turn, verify intermediate results, apply any logic required to set parameters, decide best-fit results, merge in data from other catalogs and to format convenient text and web-based output. We will outline this processing pipeline design and challenges, discuss the scientific applications, and focus on its role in monitoring on-orbit observatory performance.