Evaluating user experience (UX) with automated computational methods has gained increasing attention, supported by empirical evidence from UXBench. However, binary preference prediction provides limited insight, while relying on a single user-agnostic reward model overlooks the inherent heterogeneity of users, whose expectations can differ substantially. In this paper, we present UXBench Pro, comprising 1{,}000 test instances derived from real user interactions across 12 task scenarios and 82 domains. Each instance is paired with a FACTORS user profile that characterizes the user through seven interpretable behavioral facets, differentiating user groups. To provide richer evaluation insights, we introduce a dual-perspective paradigm that combines a personalized User Reward Model (URM) for third-person judgment with Sim4Eval, a user simulator that enables multi-turn interactions and provides first-person evaluation across four cognitive state dimensions. To assess the reliability of these based evaluators, we further introduce two meta-benchmarks, URMBench and USimBench, that evaluate how faithfully they reproduce real human preferences and behaviors. Extensive experiments reveal seven key findings that highlight the importance of user modeling and multi-perspective evaluation, offering a fresh perspective on user-centric benchmarking and motivating personalized model optimization.

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