Older adults commonly experience chronic conditions such as pain and sleep disturbances and may consider cannabidiol for symptom management. Safe use requires appropriate dosing, careful titration, and awareness of drug interactions, yet stigma and limited health literacy often limit understanding. Conversational artificial intelligence systems based on large language models and retrieval-augmented generation may support cannabidiol education, but their safety and reliability remain insufficiently evaluated. This study developed a retrieval-augmented large language model framework that combines structured prompt engineering with curated cannabidiol evidence to generate context-aware guidance for older adults, including those with cognitive impairment. We also proposed an automated, annotation-free evaluation framework to benchmark leading standalone and retrieval-augmented models in the absence of standardized benchmarks. Sixty-four diverse user scenarios were generated by varying symptoms, preferences, cognitive status, demographics, comorbidities, medications, cannabis history, and caregiver support. Multiple state-of-the-art models were evaluated, including a novel ensemble retrieval architecture that integrates multiple retrieval systems. Across three automated evaluation strategies, retrieval-augmented models consistently produced more cautious and guideline-aligned recommendations than standalone models, with the ensemble approach performing best. These findings demonstrate that structured retrieval improves the reliability and safety of AI-driven cannabidiol education and provide a reproducible framework for evaluating AI tools used in sensitive health contexts.