The objective in this chapter is to identify the most relevant benefits of medicare advantage health plans that drive membership and market share. We explore plans operating in Connecticut from September 2019 to 2022. A dataset of benefits from publicly available data sources is created for this chapter, and PCR is applied to capture the correlation between the extracted features and market share, avoiding the multicollinearity and overparameterization problems. We identify a degree of correlation between market share and prominent benefits and features such as drug coverage, star ratings, and dietary benefits, among others.