In collaboration with Maya Design Group, we have developed an initial vision of such a collaborative scheduling environment. "Ditops-Visage" is an advanced system for development and management of complex transportation schedules. Users utilize advanced data exploration and visualization tools (Visage) to interpret scheduler results, assess implications with respect to other, external data sources and planning perspectives, and to focus (re)scheduling actions. An incremental reactive scheduler (Ditops) provides flexible schedule revision and (re)optimization capabilities for responding to user inputs. A demonstration of the integrated Ditops-Visage prototype showing a deployment re-planning scenario has been developed for DARPA's JFACC program.