Working on getting Windows 8 to recognize a playlist.
The Problem: A playlist when exported to the music folder will show up in the Music App and the names will appear in that playlist but the files are unavailable.
Research: The Music app is just displaying the song name from the playlist it is not checking against it's own library. Therefore the presence of a playlist just means that there is a text file on the drive.
Short version until I write this:
Use MusicBee to create and sync (need to write how I got that working as well)
For musicbee to easily update your music map the music folder on your tablet, over the network, to a local drive.
Tell musicbee to use that drive as a device.
Use Media Monkey instead of the stock Xbox P.O.S.
Drop playlists into sub folder of music folder D:\Music\Playlists
Absolutely address the playlist for the tablet i.e. D:\Music\
Under settings for device, Device settings tab, path prefix for tracks
So the exported playlist contains links that look like: D:\Music\Beatles\1962-1966\Beatles - Hard day's night.mp3
Find this by looking at the exported playlist, on the tablet, with notepad or pspad.