This paper explores the conditions and theoretical issues of literary translation, with specific reference to an "assessment project of English literary classics in translation." It consists of three parts: the internal and external conditions of literary translation in Korea, a brief report of the project and its findings with reference to the translations of Pride and Prejudice, and lastly, some theoretical issues involved in such an assessment. Translation has been a significant factor in the formation of modern Korea. However, the conditions of translation and the general quality of translated texts still leaves much room for improvement. The practical purport of the project is to identify recommendable translations of English classic novels, but in the case of the 34 translated versions of Austen's text, no single recommendable text was to be found. Such a result shows that the quality issue is still crucial, at least in the context of Korean translation, in spite of the paradigm shift we are witnessing now in Translation Studies from an evaluative approach to a descriptive one. This paper ends by reflecting on the categories of evaluation and faithfulness in terms of their theoretical and practical implications.