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The efficiency of hyperparameter optimization (HPO) is critical for deep learning, yet state-of-the-art methods share a fundamental flaw: they are difficulty-agnostic, treating all hyperparameter configurations homogeneously. This approach leads to inefficient resource allocation, wasting budget in simple regions while under-exploring complex, rugged landscapes, and thereby critically undermining both search efficiency and final performance. To address this universal challenge, we introduce DABO, a framework that pioneers difficulty-aware tuning within the efficient context of Freeze-Thaw Bayesian Optimization. We first model optimization difficulty hierarchically. Then, departing from hand-crafted priors, we train a conditional diffusion model on 120,000 real learning curves, generating synthetic data with 2.3xhigher fidelity. This data trains our difficulty-aware surrogate model and acquisition function to dynamically adapt the search strategy. Across 75 tasks, DABO reduces regret by 11-18% compared to the leading difficulty-agnostic method, ifBO. Our work establishes a new paradigm for HPO, shifting the focus from configuration-centric to difficulty-aware resource allocation to enable more robust and efficient optimization.