A package manager (PM) is crucial to most technology stacks, acting as a broker to ensure that a verified dependency package is correctly installed, configured, or removed from an application. Diversity in technology stacks has led to dozens of PMs with various features. While recent studies have shown that developers struggle to migrate their dependencies, the common assumption is that PMs are used without any issue. In this study, we explore sixteen PMs to understand whether their features correlate with the experience of their users. By studying experience through the questions that developers ask on the question-and-answer site Stack Overflow, we find that developer questions are grouped into three themes (i.e., PM management, Input-Output, and Package Usage). Our analysis results indicate that specific features are correlated with the user experience. Our work lays out future directions to investigate the trade-offs involved in designing the ideal PM.