I've got ~140GB of music, and always use Zune and its autoplaylists on my PC, but I could never find a good way to directly sync all of the songs from a playlist like we did with WP7.
So, I actually made my own program to read my Zune playlists and copy those songs into a separate folder (one for DRM Xbox Music songs, and one for non-DRM songs) - from there I just drag and drop the non-DRM songs with Explorer to my phone, then use the Windows Phone "Metro" app to sync the DRM protected files. It works well enough - and I'm not sure whether there's any other way to go about this yet (anyone else know?).
I'll be using Zune on my PC until they get a proper replacement for it and all of its features, so it feels like it was worth the effort (which really wasn't too much).