Flexible and wearable electronics demand transistor technologies that can sustain stable performance under extreme mechanical deformation. In this work, we propose a quantitative benchmarking framework for strain resilience in organic thin-film transistors (OTFTs), introducing three normalized metrics: degradation factor (DF), quantifying drain-current loss under strain; the mobility factor (MF), representing the rate of charge-transport degradation per unit strain; and the strain-stability window (SSW), defining the maximum strain range within which devices remain in the safe operating zone (DF < 15%). Using Silvaco Victory TCAD, we systematically investigate the strain-dependent behavior of single-dielectric (Al2O3) and hybrid-dielectric (Al2O3/PVP) OTFTs under both compressive (concave) and tensile (convex) bending with radii from 8 to 1 μm. Results show that hybrid-dielectric OTFTs exhibit superior strain tolerance, with a DF of only 9% under 9.85% tensile strain, compared with 25% for single-dielectric devices. Furthermore, hybrid devices show a markedly lower MF (−3%/strain compressive and −1.9%/strain tensile) compared with single-dielectric OTFTs (−6%/strain compressive and −5%/strain tensile). Beyond confirming the mechanical advantages of hybrid dielectrics, our study demonstrates that strain-stability quantifiers provide a universal method to benchmark flexible OTFT reliability, bridging device physics with practical requirements of wearable bioelectronics. These findings establish hybrid Al2O3/PVP dielectrics not only as performance enhancers but also as reliable design enablers for next-generation strain-resilient organic electronics.