Washington D.C. is home to many historic elm corridors managed in close partnership between numerous urban forestry stakeholders. In recent years, the city's elms have been used as part of streetscape revitalization initiatives due to their quick-growing nature. The use of a popular Ulmus americana cultivar, Princeton, has brought about notable challenges in urban tree management. From the nursery to the tree box and even ten years later, these elms have required consistent attention in order to adequately train the form to achieve a sustainable canopy while minimizing structural defects. Two such plantings are explored, both with hand-selected trees from the same stock and nursery. These serve to highlight the differences between traditional urban forestry plantings and those under constant and careful scrutiny.