CAD segmentation datasets are predominantly synthetic or automatically labelled, leaving it unclear how well existing methods transfer to real-world engineering tasks. Fastener-relevant hole detection represents one such task, requiring human annotation and exhibiting greater geometric complexity than commonly used benchmarks. We address this gap through three main contributions. First, we develop two task-specific rule-based methods, one graph-wire-search and one multi-view based, and complement them with a human-annotated benchmark dataset derived from engineering CAD data that also enables training of UV-Net and AAGNet, representative learning-based approaches for B-Rep segmentation. Second, we conduct an extensive experimental study including parameter optimisation, evaluation on our benchmark dataset, cross-domain generalisation on a synthetic dataset, and an assessment of the feasibility of the approaches at varying dataset sizes and IoU thresholds. Third, we provide evidence-based insights into the strengths and limitations of different approaches: rule-based methods generalise well without training data, with the graph-wire-search method favouring recall and the multi-view method favouring precision, whereas learning-based methods achieve strong performance with sufficient annotations but exhibit reduced robustness under domain shift. These findings highlight trade-offs between data requirements, and robustness, and provide guidance not only for hole detection, but more broadly for real-world CAD segmentation tasks.

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