Learning human preferences in language models remains fundamentally challenging, as reward modeling relies on subtle, subjective comparisons or shades of gray rather than clear-cut labels. This study investigates the limits of current approaches and proposes a feature-augmented framework to better capture the multidimensional nature of human judgment. Using the Anthropic HHRLHF dataset, we evaluate ten diverse large language models LLMs under a standard pairwise preference setting, where baseline performance remains below 0.74 ROC AUC, highlighting the difficulty of the task. To address this, we enrich textual representations with interpretable signals: response length, refusal indicators, toxicity scores and prompt response semantic similarity, enabling models to explicitly capture key aspects of helpfulness, safety and relevance. The proposed hybrid approach yields consistent improvements across all models, achieving up to 0.84 ROC AUC and significantly higher pairwise accuracy, with DeBERTav3Large demonstrating the best performance. Beyond accuracy, we integrate SHAP and LIME to provide fine-grained interpretability, revealing that model decisions depend on contextualized safety and supportive framing rather than isolated keywords. We further analyze bias amplification, showing that while individual features have weak marginal effects, their interactions influence preference learning.