Some school districts have centralized school operations as a means to ensure universal access to schools of choice. Yet, centralization can infringe on charter school autonomy. We explore how district and charter school leaders in three contexts perceive and negotiate the trade-offs between centralized versus school-based autonomy. We find that decision-making and governance of student transportation are inherently place-specific, with conditions of history, geography, infrastructure, and state governance dominating leaders' preferences. Therefore, despite the recognized benefits, school leaders maintain vastly different perspectives about the feasibility and appeal of centralized transportation within the charter sector.