Creating an orthographic system is a huge and daunting task; however even working with a previously established orthography comes with its own set of challenges. Our project involves developing materials for learners of the Uto-Aztecan language Hiaki (also written variously as Yaqui, Jiaki, Yoeme). Here we outline some of the challenges and choices we have faced in implementing the established orthographic system in a consistent and useful way while dealing sensitively with the interests of a) learners of the language, and b) existing communities of speakers. We focus on three primary areas: the tension between underlying and surface representations with regard to vowel length and pitch accent placement, dialect differences and sound changes, and cliticization and the representation of word boundaries. Throughout the relationship between learner needs and providing a complete and accurate representation for the community is highlighted.