Developers consistently use version constraints to specify acceptable versions of the dependencies for their project. \emph{Pinning} dependencies can reduce the likelihood of breaking changes, but comes with a cost of manually managing the replacement of outdated and vulnerable dependencies. On the other hand, \emph{floating} can be used to automatically get bug fixes and security fixes, but comes with the risk of breaking changes. Security practitioners advocate \emph{pinning} dependencies to prevent against software supply chain attacks, e.g., malicious package updates. However, since \emph{pinning} is the tightest version constraint, \emph{pinning} is the most likely to result in outdated dependencies. Nevertheless, how the likelihood of becoming outdated or vulnerable dependencies changes across version constraint types is unknown. \textit{The goal of this study is to aid developers in making an informed dependency version constraint choice by empirically evaluating the likelihood of becoming outdated or vulnerable dependencies across version constraint types at scale.} In this study, we first identify the trends in dependency version constraint usage and the patterns of version constraint type changes made by developers in the npm, PyPI, and Cargo ecosystems. We then modeled the dependency state transitions in survival analysis and estimated how the likelihood of becoming outdated or vulnerable changes when using \emph{pinning} as opposed to the rest of the version constraint types. We observe that among outdated and vulnerable dependencies, the most commonly used version constraint type is \emph{floating-minor}, with \emph{pinning} being the next most common. We also find that \emph{floating-major} is the least likely to result in outdated and \emph{floating-minor} is the least likely to result in vulnerable dependencies. Based on our findings, we recommend that developers use any kind of \emph{floating} constraint with lockfiles to balance the tradeoffs of \emph{pinning} and \emph{floating}.