Large Language Models (LLMs) have demonstrated impressive capabilities in role-playing scenarios, particularly in simulating domain-specific experts using tailored prompts. This ability enables LLMs to adopt the persona of individuals with specific backgrounds, offering a cost-effective and efficient alternative to traditional, resource-intensive user studies. By mimicking human behavior, LLMs can anticipate responses based on concrete demographic or professional profiles. In this paper, we evaluate the effectiveness of LLMs in simulating individuals with diverse backgrounds and analyze the consistency of these simulated behaviors compared to real-world outcomes. In particular, we explore the potential of LLMs to interpret and respond to discharge summaries provided to patients leaving the Intensive Care Unit (ICU). We evaluate and compare with human responses the comprehensibility of discharge summaries among individuals with varying educational backgrounds, using this analysis to assess the strengths and limitations of LLM-driven simulations. Notably, when LLMs are primed with educational background information, they deliver accurate and actionable medical guidance 88% of the time. However, when other information is provided, performance significantly drops, falling below random chance levels. This preliminary study shows the potential benefits and pitfalls of automatically generating patient-specific health information from diverse populations. While LLMs show promise in simulating health personas, our results highlight critical gaps that must be addressed before they can be reliably used in clinical settings. Our findings suggest that a straightforward query-response model could outperform a more tailored approach in delivering health information. This is a crucial first step in understanding how LLMs can be optimized for personalized health communication while maintaining accuracy.