Recent approaches in personalized reward modeling have primarily focused on leveraging user interaction history to align model judgments with individual preferences. However, existing approaches largely treat user context as a static or implicit conditioning signal, failing to capture the dynamic and multi-faceted nature of human judgment. In this paper, we propose P-Check, a novel personalized reward modeling framework, designed to train a plug-and-play checklist generator that synthesizes dynamic evaluation criteria for guiding the reward prediction. To better align these checklists with personalized nuances, we introduce Preference-Contrastive Criterion Weighting, a training strategy that assigns saliency scores to criteria based on their discriminative power for personalized judgment. We conduct extensive experiments and demonstrate that P-Check not only improves reward accuracy but also enhances downstream personalized generation, and remains robust in OOD scenarios.