Metal coordination can substantially change the biological behavior of Schiff-base ligands, but antimicrobial inhibition, cancer-cell cytotoxicity, antioxidant response, DFT descriptors, and molecular docking are often interpreted as though they identify the same active compound. The reliability of that assumption was examined for a four-member tridentate imine series comprising H2B and its ZrO(IV), VO(IV), and Pd(II) complexes. Numerical endpoints for inhibition zones and minimum inhibitory concentrations against Escherichia coli, Micrococcus luteus, Aspergillus flavus, and Geotrichum candidum; HCT-116 IC50 values; DPPH antioxidant ordering; DFT-derived reactivity descriptors; and docking energies for the 6KQ9 and 1R4U receptor models were harmonized into direction-corrected scores. Metalation improved the phenotypic profile relative to H2B, with PdB giving the highest mean inhibition zone, highest mean activity index, lowest HCT-116 IC50 among the complexes, and strongest ordinal DPPH response. In contrast, VOB had the most favorable docking energies for both receptor models. The phenotype composite ranked PdB > ZrOB > VOB > H2B, whereas the docking composite ranked VOB > ZrOB > PdB > H2B. The resulting rank inversion demonstrates that docking affinity is not a direct surrogate for whole-cell antimicrobial or HCT-116 cytotoxic potency in this metal-complex panel. Sensitivity analysis further showed that PdB remains the preferred phenotypic candidate unless docking receives more than approximately one-third of the total prioritization weight, after which VOB becomes dominant. The work establishes a reproducible endpoint-resolved strategy for distinguishing phenotypic leads from receptor-binding candidates and defines the additional validation needed before mechanistic or therapeutic conclusions are drawn from compact bioinorganic screening datasets.