I just listened to them all mostly through to figure this out, still a tentative ranking as I tend to change my mind every time re-listen to them
1) Tracker, Down the Road Wherever, and Sailing to Philadelphia
2) The Ragpicker's Dream, Privateering, and Get Lucky
3) Golden Heart, Kill to Get Crimson, Shangri-La
I love DTRW, guess I'll see how it stands over time, but it's at the top of my list now. Drover's Road is one of my favorite songs now, OSAAT is wonderful, Matchstick Man is a more autobiographical version of Heart of Oak which I love. Thrilled with DTRW overall, it's a wonderful new album. And It's gotten my dad, who hasn't paid attention to MK since a few popular songs in the DS days and hasn't listened to his solo stuff, to start listening (first I introduced him to Sailing to Philadelphia which he also liked, but he loves this one)
Even the bottom tier here doesn't mean I don't like the albums, just a bit less than others. Although KTGC I don't listen to much besides In the Sky. Shangri-La I didn't like after a couple listens and just listened to it again and now I like it more... I guess I just had to turn the volume up, go figure