I have some syncing bugs in 2.0 that have been lingering for a while because I was never able to reproduce them myself. Mostly stuff like you’re describing where updated playlists don’t update in Rekord Buddy.
That’s one of the reasons I’m switching to a different workflow in 2.1 where users can control for themselves what gets imported and what gets exported, making it easier to identify issues like this.
Quickest diagnostic right now would be to try the latest 2.1 beta and see if you see this issue there too. If you don’t I would suggest sticking with the beta as it’s near release and the issues with it have been minimal so far. If you DO see the problem then contact me via support so I can look into it with you and fix it.