Moonshine/Timberwolf
By 4300 AD, the proto-Moonshine language had a consonant inventory of:
Labials: p m f w Alveolars: t n s l r Palataloids: č ň š ž y Velars: k ŋ h g
Vowels were
High tone à ì ù ə̀ Low tone a i u ə Long ā ī ū ə̄
Proto-Moonshine (4300) to Timberwolf (6843)
This language is probably spoken in the mountains at the extreme southern edge of Moonshine territory. It may even be "Oscar". It is very conservative, perhaps with sound changes held in check by gender-based speech registers, as in Middlesex.
The target phonology retains three tones and has five or six vowels, the new vowels resulting from smoothing of diphthongs. Note that the diphthongs of PMS were linked to tone and thus a simple shift will not produce new vowels for all three tones. Consonants shifts will likely be very sparse, and may focus on elimination of labialization.
This is the same language that in my childhood I had planned to evolve into a language entirely without consonants, with the tones and vowels carrying the information. I am typing this up here as a reminder of its cultural association.