Generative AI is increasingly used to accelerate assessment content development, yet its effectiveness for generating content used in complex assessment tasks for knowledge-rich domains such as medical education is unclear. This study evaluates automated LLM-supported workflows for generating patient-centered communication assessment items that allow students to practice their communication skills. We compared two content generation approaches—constrained linear and exploratory branching—each implemented with and without anchoring in vetted multiple-choice questions (MCQs). Ten subject-matter experts (SMEs) evaluated 80 communication items across six quality dimensions using structured rubrics. The constrained linear approach yielded better ratings than exploratory branching approaches, particularly for medical accuracy and alignment with learning objectives and patient-centered behaviors. MCQ anchoring did not improve medical accuracy. Only a minority of items met all criteria without requiring revision, and no items were unanimously approved by all SMEs. These findings underscore the importance of workflow design in LLM-supported assessment content generation, the continued need for human oversight, and the current limitations of automated content generation in medical education.