As service robots become more capable of autonomous behaviors, it becomes increasingly important to consider how people communicate with a robot what task it should perform and how to do the task. Accordingly, there has been a rise in attention to end-user development (EUD) interfaces, which enable non-roboticist end users to specify tasks for autonomous robots to perform. However, state-of-the-art EUD interfaces are often constrained through simplified domains or restrictive end-user interaction. Motivated by prior qualitative design work that explores how to integrate a care robot in an assisted living community, we discuss the challenges of EUD in this complex domain. One set of challenges stems from different user-facing representations, e.g., certain tasks may lend themselves better to rule-based trigger-action representations, whereas other tasks may be easier to specify via sequences of actions. The other stems from considering the needs of multiple stakeholders, e.g., caregivers and residents of the facility may all create tasks for the robot, but the robot may not be able to share information about all tasks with all residents due to privacy concerns. We present scenarios that illustrate these challenges and also discuss possible solutions.