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The Technical Debt Assessment skill provides a systematic framework for Claude to analyze software projects for hidden technical debt and its long-term impact. By utilizing the Fowler Debt Quadrant and a financial Principal-Interest model, it allows teams to go beyond simple code smells to calculate the actual cost of delay and the break-even point for refactoring. This skill helps developers move from intuitive concerns about code quality to objective proofs of business impact by quantifying productivity loss, quality risks, and velocity slowdowns associated with specific architectural or code-level issues.