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Open circular holes are an important design feature, for instance in bolted joint connections. However, stress concentrations arise whose magnitude depends on the material anisotropy and on the defect size relative to the outer finite plate dimensions. To design both safe and light-weight optimal structures, precise means for the assessment are crucial. These can be based on analytical methods providing efficient computation. For this purpose, the focus of the present paper is to provide a comprehensive stress and failure analysis framework based on analytical methods, which is also suitable for use in industry contexts. The stress field for the orthotropic finite-width open-hole problem under uniform tension is derived using the complex potential method. The results are eventually validated against Finite-Element analyses revealing excellent agreement. Then, a failure analysis to predict brittle crack initiation is conducted by means of the Theory of Critical Distances and Finite Fracture Mechanics. These failure concepts of different modelling complexity are compared to each other and validated against experimental data. The size effect is captured, and in this context, the influence of finite width on the effective failure load reduction is investigated.