A personal opinion on the two latest albums (which I consider her two best, so far):
I think, with "Storyteller", Carrie was already moving in some of the directions she brought to fruition in "Cry Pretty". H, TGYTIA, & WINKIAW were all personal songs, and all were Carrie co-writes, Three may not seem a particularly high number, but I don't think they are ever likely to predominate on one of her albums, and I think this was a side of her inspiration that she wanted to demonstrate. TGYTIA was the one that showed the most vulnerability and introspection (and the strongest song of the three, in my opinion). I see it as the one closest to the direction she explored more fully in "Cry Pretty".
There were four "picks" (not co-writes) that I think showed aspects of contemporary Country that Carrie may have wanted to support. In two of those, Carrie picked young women who had appeared on Song Suffragettes: Sarah Haze (Relapse) and Kat Higgins (Mexico). These were both musically Progressive songs, which drew on General Music influences - and I think Carrie probably wanted to support both "emerging" female artists, and the modern crossover blending in the genre's sounds.
The other two, I feel, balanced that, with a timeless appeal, echoing Country roots - and the search for that balance is a characteristic I find in Carrie's music through much of her career. CCA was built on a premise that stylistically & thematically gave clear nods to Bobbie Gentry - an artist whose career in the 1960s had parallels with Carrie's own, in her use of tradition within a contemporary context, her storytelling and her international appeal. LINLYA was written by the Love Junkies - arguably one of the most respected songwriting combinations in the genre today, all of whom combine tradition with contemporary relevance successfully. This song was a bold choice by Carrie, in which she gave what I see as one of her best performances - aimed more at exploring the emotional potential of a lyric, rather than at transient radio appeal.
Add to those "Smoke Break" - which I see as one of Carrie's best co-writes - and we have what I consider another forerunner of parts of "Cry Pretty", an "issue" song that uses character to express social awareness.
Coming to "Cry Pretty" itself, I see Carrie making an album of a type which I believe she probably wanted to make, but was probably not able to quite achieve earlier, when she had to rely on other producers. In that sense, I see her co-production role as a particularly important artistic development in her career. That is not to say that I expect future albums to be like "Cry Pretty" - they are likely to vary, according to changing moods and circumstances. But I do see that album as having a liberating effect in encouraging new avenues of expression. Partly, I see the album as rooted in a particularly traumatic time of Carrie's life - we have heard of the miscarriages, but we cannot know the full depth of her feelings (and rightly so), but it seems that the title song, "Low" and "Ghosts" drew on the experiences of that time (and those songs are ones that I see as among the strongest of her career.) That aspect stemmed from a particular time - but there are other themes in the album that strike me as more general in Carrie's musical approach, One is the interplay between tradition and progression that I've mentioned before - and which I see as more evident in Carrie's work than in many of the other chart artists of today. "Ghosts" specifically names some of her forerunners - and is unusual in the fact that family members or associates of those legends chose to play on it in backing her. But the link to Hank Williams is particularly apparent in "Low" (and also seems to occur, more obliquely, elsewhere).
Other examples of the tradition-progression interplay, which I find particularly striking, is the use of a timeless Country Waltz rhythm in the album's title track, and the heavy use of resophonic instruments (dobro and pedal steel) in the more "Pop" influenced songs. This incorporation of tradition is, again, something I notice more in Carrie than in many other chart artists today.
Finally, the "issue" songs, especially "The Bullet" and "Spinning Bottles", come across as more developed on this album, and this is something that may continue in future (though probably only in one or two songs on albums that will continue to be mixed in theme)