Many Postgres users do not upgrade to the latest version due to two core issues: Postgres works well and upgrades are difficult. While older versions of Postgres are capable for most developers' needs, newer versions offer significant performance improvements and new features. However, major updates can be time-consuming and resource-intensive, leading many organizations to postpone upgrades until necessary. Despite the challenges, it is recommended to upgrade regularly to benefit from improved functionality and compatibility with new tools and frameworks.