The management of third-party package dependencies is crucial to most technology stacks, with package managers acting as brokers to ensure that a verified package is correctly installed, configured, or removed from an application. Diversity in technology stacks has led to dozens of package ecosystems with their own management features. While recent studies have shown that developers struggle to migrate their dependencies, the common assumption is that package ecosystems are used without any issue. In this study, we explore 13 package ecosystems 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., Package management, Input-Output, and Package Usage). Our preliminary analysis indicates 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 package ecosystem.