A usually mentioned problem in Digital Humanities (DH) is the difficult fit between Humanities research questions and DH methodologies. This chapter is therefore configured as a meta-chapter that explains the problems and strategies when exploring the multilingual repository of Philippine periodicals constructed within the project “Strenghthening Digital Research at the UP System” in order to research the evolution of the image of China in these periodicals. The two main challenges found for analysing the periodicals to find an answer have been (1) Problematic OCRs, (2) Research across multi-lingual publications. The chapter lists literature and research projects that have approached similar questions and challenges in comparable corpora. Some suggestions of tools to address them will also be provided.