This study describes significant issues and learnings identified by 26 school faculties engaged in site-based, faculty-led reform initiatives over a 5-year period during participation in the National Education Association's Mastery in Learning (MIL) Project. A representative sample of MIL sites is utilized to reframe issues and learnings into dilemmas. The paper explores: (1) the concept of dilemmas in educational decision making; (2) the background of MIL; (3) cross-project data (timelines, end-of-project interview transcripts, and transcripts of narratives); (4) six sites as exemplars in identifying faculty-led school restructuring; (5) each site's restructuring endeavors; (6) a categorized list of dilemmas derived from self-report data; and (7) utilization of a dilemma framework as a component of faculty development and collaboration. Included are tables listing frequency and "globalness" of issues such as percentage of disruptions, personal learnings, and advice for others and a figure describing dilemmas expressed by MIL participants. Dilemmas of Schooling (from Berlak & Berlak, 1981), a sample timeline, and an end-of-project interview protocol are appended. (LL)