Metrics and frameworks to quantifiably assess security measures have arisen from needs of three distinct research communities - statistical measures from the intrusion detection and prevention literature, evaluation of cyber exercises, e.g.,red-team and capture-the-flag competitions, and economic analyses addressing cost-versus-security tradeoffs. In this paper we provide two primary contributions to the security evaluation literature - a representative survey, and a novel framework for evaluating security that is flexible, applicable to all three use cases, and readily interpretable. In our survey of the literature we identify the distinct themes from each community's evaluation procedures side by side and flesh out the drawbacks and benefits of each. The evaluation framework we propose includes comprehensively modeling the resource, labor, and attack costs in dollars incurred based on expected resource usage, accuracy metrics, and time. This framework provides a unified approach in that it incorporates the accuracy and performance metrics, which dominate intrusion detection evaluation, the time to detection and impact to data and resources of an attack, favored by educational competitions' metrics, and the monetary cost of many essential security components used in financial analysis. Moreover, it is flexible enough to accommodate each use case, easily interpretable and comparable, and comprehensive in terms of costs considered.Finally, we provide two examples of the framework applied to real-world use cases. Overall, we provide a survey and a grounded, flexible framework with multiple concrete examples for evaluating security which can address the needs of three currently distinct communities.