Transmasculine individuals undergoing testosterone hormone replacement therapy (HRT) typically experience a lowering of vocal pitch over the course of the first year, which has been linked to increased satisfaction with their voices. This work addresses two concerns: first, that effects of HRT on vocal characteristics other than pitch are understudied; second, that the degree of individual variation in speakers' vocal goals, identities, and circumstances is such that purely-quantitative metrics do not provide a complete picture of how these acoustic changes contribute to overall vocal satisfaction. This longitudinal study examines change in habitual pitch, vocal range, vowel formant frequencies, and estimated vocal tract length in 18 transmasculine English speakers over approximately the first year of HRT. It further investigates speaker satisfaction through a combination of surveys and qualitative interviews. Speakers exhibited the expected lowering of habitual pitch and floor; most saw no perceptually salient narrowing of range in semitones. Change in formant frequencies was highly variable, with an overall trend towards lower F1 and F2 alongside persistent and unexpected raising of F3. Satisfaction was not guaranteed for speakers following the first year of HRT. However, the reasons cited behind dissatisfaction were were largely unique to the individual, contingent on both self- and external perception of vocal gender as well as the acoustic change seen. Work to improve vocal satisfaction in transmasculine speakers must not only take acoustic properties other than pitch into account, but consider the individual circumstances of those who express dissatisfaction.