Auditory headsets capable of actively or passively intermixing both real and virtual sounds are in-part acoustically transparent. This paper explores the consequences of acoustic transparency, both on the perception of virtual audio content, given the presence of a real-world auditory backdrop, and more broadly in facilitating a wearable, personal, private, always-available soundspace. We experimentally compare passive acoustically transparent, and active noise cancelling, orientation-tracked auditory headsets across a range of content types, both indoors and outdoors for validity. Our results show differences in terms of presence, realness and externalization for select content types. Via interviews and a survey, we discuss attitudes toward acoustic transparency (e.g. being perceived as safer), the potential shifts in audio usage that might be precipitated by adoption, and reflect on how such headsets and experiences fit within the area of Mixed Reality.