The transition into medical school is challenging: students must adapt to vastly different academic demands, learning environments, and expectations despite prior success. Many enter with limited understanding of evidence-based learning strategies, institutional resources, and the realities of medical education, spending valuable time navigating study tools, learning systems, third-party resources, and emerging technologies through trial and error. To reduce these barriers, we developed near-peer educational resources to orient incoming students and promote effective study strategies. As second-year medical students, we collaborated with faculty to create a pre-matriculation resource series within our institution's Canvas readiness community. Videos covered the medical school journey, active learning, effective Anki use, responsible AI use, and navigation of institutional and third-party resources. Content was informed by feedback from second-year students (n = 42) on transition challenges. Materials were distributed to incoming students (n = 160) before orientation, with engagement and perceptions evaluated via utilization metrics and surveys. The project continues through longitudinal near-peer "study spotlights" highlighting diverse learning approaches tailored to curricular phases. Preliminary data show positive perceptions, with all users rating the series moderately to extremely beneficial. Early feedback suggests students value practical demonstrations of study tools, candid discussion of the transition, and insights tailored to the local curriculum, as early curricula align poorly with third-party resources. Ongoing evaluation will inform future content and programming, including upperclassman panels. Near-peer resources may reduce transition barriers by providing timely guidance on learning strategies, academic resources, and professional development, helping students adapt, build confidence, and establish foundations for long-term academic success.