Supervised methods for object delineation in remote sensing require labeled ground-truth data. Gathering sufficient high quality ground-truth data is difficult, especially when targets are of irregular shape or difficult to distinguish from background or neighboring objects. Tree crown delineation provides key information from remote sensing images for forestry, ecology, and management. However, tree crowns in remote sensing imagery are often difficult to label and annotate due to irregular shape, overlapping canopies, shadowing, and indistinct edges. There are also multiple approaches to annotation in this field (e.g., rectangular boxes vs. convex polygons) that further contribute to annotation imprecision. However, current evaluation methods do not account for this uncertainty in annotations, and quantitative metrics for evaluation can vary across multiple annotators.