Software readability is greatly improved when programs include descriptive comments in a predictable, standardized format. Program headers that describe software requirements, author, creation date, versioning history, caveats, and other metadata are a common method to facilitate a greater understanding of software objectives, strengths, weaknesses, and prerequisites. Moreover, when program headers are standardized, they are not only more readable to developers but also to parsing algorithms that can automatically extract metadata for analysis or archival. Comments throughout software can also improve its readability and, when constructed in a standardized format, can be parsed automatically and saved in control tables. This text introduces a standardized commenting methodology that enables both qualitative and quantitative comments to be parsed from SAS® software headers and body. A configuration file defines comment formatting and content and provides a flexible, scalable, reusable, data-driven SAS macro-based solution. This text demonstrates one use case for this methodology in which software technical debt and risk are assessed via both qualitative (e.g., risk description, proposed risk resolution) and quantitative (e.g., risk severity, risk probability, likelihood of risk discovery, ease of risk mitigation) metadata and metrics included within SAS comments. The comment interpreter dynamically identifies and parses all SAS program files and SAS Enterprise Guide project files (including imbedded SAS programs therein) within one or more folders to produce a comprehensive, quantifiable risk register. This data-driven documentation, generated with push-button simplicity, enables SAS practitioners to better understand and make decisions about technical debt and risk, including at the program, project, developer, team, and organizational levels.