Every family of significant wealth eventually accumulates holdings that no longer fit cleanly into a portfolio review. A minority stake in a company long since sold. A ranch or vineyard bought for a purpose the family has since outgrown. Holdings that predate the current strategy and are rarely reassessed as rigorously as the liquid portfolio. The result is a familiar pattern. Legacy assets persist by default rather than by decision, consuming capital, management attention, and a disproportionate share of family conflict. In this white paper, we introduce a structured eight-dimension diagnostic to assess whether to hold, enhance, or sell.