With increasing deployment of Large Language Models (LLMs) in the finance domain, LLMs are increasingly expected to parse complex regulatory disclosures. However, existing benchmarks often focus on isolated details, failing to reflect the complexity of professional analysis that requires synthesizing information across multiple documents, reporting periods, and corporate entities. They do not distinguish whether errors stem from retrieval failures, generation flaws, finance-specific reasoning mistakes, or misunderstanding of the query or context. This makes it difficult to pinpoint performance bottlenecks. To bridge these gaps, we introduce Fin-RATE, a benchmark built on U.S. Securities and Exchange Commission (SEC) filings and mirror financial analyst workflows through three pathways: detail-oriented reasoning within individual disclosures, cross-entity comparison under shared topics, and longitudinal tracking of the same firm across reporting periods. We benchmark 17 leading LLMs, spanning open-source, closed-source, and finance-specialized models, under both ground-truth context and retrieval-augmented settings. Results show substantial performance degradation, with accuracy dropping by 18.60% and 14.35% as tasks shift from single-document reasoning to longitudinal and cross-entity analysis. This is driven by rising comparison hallucinations, time and entity mismatches, and mirrored by declines in reasoning and factuality--limitations that prior benchmarks have yet to formally categorize or quantify.