We give a narrative description of our ten-year path into the elaborate tonal systems of the Chatino languages (Otomanguean; Oaxaca, Mexico), and of some of the methods we have used and recommend, illustrated with specific examples. The work, ongoing at the time of writing, began when one of us (Cruz), a native speaker of San Juan Quiahije Chatino, entered the University of Texas at Austin as a Ph.D. student and formed, together with the other of us (Woodbury), a professor there, the Chatino Language Documentation Project, ultimately incorporating five other Ph.D. students and two other senior researchers. We argue for the importance of an interplay among speaker and non-speaker perspectives over the long course of work; a mix of introspection, hypothesis-testing, natural speech recording, transcription, translation, grammatical analysis, and dictionary-making as research methods and activities; an emphasis on community training as an active research context; the simultaneous study of many varieties within a close-knit language family to leverage progress; and the use of historical-comparative methods to get to know tonal systems and the roles they play at a deeper level.