Navigating and transporting efficiently within small campuses presents unique challenges, often stemming from unclear routing information and inefficiencies in existing systems. This study investigates these issues to highlight the critical need for innovative solutions. Through a comprehensive survey conducted across a compact, interconnected campus, key pain points in current navigation and transportation frameworks were identified. The survey explored user experiences and gathered insights on desired features, emphasizing the integration of landmark-based navigation and optimized vehicle allocation systems. Results reveal a strong demand for context-aware navigation, reduced wait times for intra-campus transportation, and real-time updates for both navigation and vehicle allocation. Participants prioritized clarity in wayfinding and systems tailored to campus-specific landmarks to enhance user experience. These findings underscore the need for advanced, context-sensitive algorithms and technologies to address the unique challenges of small campus environments. This study provides foundational insights to inform the design and implementation of next-generation navigation and transportation systems.