I have googled the issue but I couldn't find a fix and I really don't understand the problem. I'm sorry if the solution is in another post, I did try fixes from what posts I could find but it doesn't work.
I have a Sony Walkman and I have been using it with MusicBee. I had trouble with syncing when starting to use it which I don't remember exactly what the problem was, but I managed to fix it and I've been able to sync music and playlist with no problems since.
Recently I moved files in my library, taking some out of folders into the general library folder etc. I synced without noticing that it was putting the moved files as missing. Then later I also moved the entire library folder into another on my computer along with another folder, and that broke some things in the MB library.
I noticed today and I changed the paths, located missing files etc. I had a problem where all the playlists showed empty title, artist etc files but I ended up re-importing the playlists from a backup, re-syncing the pathways etc and it worked. My MB library was back to normal.
I synced with the walkman and everything showed fine on it. The missing files from the previous library moving around were there, the playlist showed exactly the same in MB and on the walkman.
Then some minutes later I added a song to an existing playlist and did another sync, and the song doesn't show on the playlist in the walkman. I tried removing all playlists from the walkman and even all files to do a clean sync but it doesn't let me delete them on the walkman. I tried duplicating the playlist but after a sync it doesn't add that playlist either. When I look up info on the playlist files on the device it says the last edit was earlier that day, there's no trace of all the sync I made since.
This is the settings I have for syncing:
-I didn't change any device setting compared to when it worked in previous sync
-the pathway to the music and playlist folders on the walkman is correct
-changing / to \ in the pathways immediately shows an error so I leave it as is (/)
-changing the playlist file type doesn't work, walkman doesn't play it and is was always set as m3u and worked that way
I'm really at loss, it literally worked then a few minutes later it didn't. Between the sync I did to fix the library problems (which worked) and the sync after adding a song to a playlist I didn't change any setting.
The times Ichanging some settings based on some posts I found but when it didn't fix the problem or added others I switched the settings back.