On the Mac side, it appears to have its own sync data in addition to the Windows sync data. It puts the Windows saves in "~/Application Support/Pillars of Eternity II" folder and the Mac saves in the "~/Application Support/Pillars of Eternity II/Saved Games". However, the game it self (both Mac & Win) load the saved games from the Saved Games folder. This causes the two platforms to be perpetually out of sync, unless you manually copy over your current saves from "~/Application Support/Pillars of Eternity II" into the Saved Games folder.
Seems to have been fixed. Thank you.
Correction, it hasn't been fixed. See video below.
Edited by warhaven, 24 May 2018 - 08:55 AM.