The deterioration of public school buildings is more prevalent in large cities that, because of funding shortfalls, have deferred maintenance and require huge sums to bring their buildings up to acceptable standards. Cities such as New York will require approximately $680 million to address the problem of deferred maintenance for needed painting, roofing, and exterior brickwork or tuck-pointing. Jonathan Kozol (1991) has presented stark contrasts in the condition of school facilities and the overall system of school funding in the American public educational system, particularly urban versus suburban schools. To illustrate this point, a study of the public schools in Washington, D.C., indicated that only 10% of the 137 schools in the District of Columbia were in good condition and 75% were in poor condition (DC Voice Ready Schools Project 2007). In this article, the author presents two case studies that grew out of his professional experiences in facility planning and efforts to address the deteriorating condition of urban public school facilities.