Passive tracking methods, such as phone and wearable sensing, have become dominant in monitoring human behaviors in modern ubiquitous computing studies. While there have been significant advances in machine-learning approaches to translate periods of raw sensor data to model momentary behaviors, (e.g., physical activity recognition), there still remains a significant gap in the translation of these sensing streams into meaningful, high-level, context-aware insights that are required for various applications (e.g., summarizing an individual's daily routine). To bridge this gap, experts often need to employ a context-driven sensemaking process in real-world studies to derive insights. This process often requires manual effort and can be challenging even for experienced researchers due to the complexity of human behaviors. We conducted three rounds of user studies with 21 experts to explore solutions to address challenges with sensemaking. We follow a human-centered design process to identify needs and design, iterate, build, and evaluate Vital Insight (VI), a novel, LLM-assisted, prototype system to enable human-in-the-loop inference (sensemaking) and visualizations of multi-modal passive sensing data from smartphones and wearables. Using the prototype as a technology probe, we observe experts' interactions with it and develop an expert sensemaking model that explains how experts move between direct data representations and AI-supported inferences to explore, question, and validate insights. Through this iterative process, we also synthesize and discuss a list of design implications for the design of future AI-augmented visualization systems to better assist experts' sensemaking processes in multi-modal health sensing data.