Between 2019 and 2025, Michigan's regulated Cannabis market evolved from an emerging industry into a more structured but still shifting economic landscape. This study examines how pricing changed over time, covering both medical Cannabis and the expansion of adult-use sales. Early on, limited licenses and regulations kept prices high, but in 2020 the emergence of adult-use Cannabis reshaped the market, driving rapid price shifts and new challenges. Unlike studies focused only on legalization's immediate impact, this research tracks long-term trends, analyzing market data and consumer behavior to identify key influences on pricing and business sustainability. The findings highlight how regulations shape industry growth, offering useful insights for policymakers, businesses, and researchers studying legal Cannabis markets. Michigan's experience provides a roadmap for other states and countries navigating legalization.