How about a DIY solution? My music is on a Linux based NAS, so this is what I've done:
1. Installed an rsync app on the android phone and copied its private key to the NAS for passwordless sync.
2. Configured MusicBee to export external playlists to a sync folder on the NAS.
3. Wrote a simple script that runs continuously on the NAS checks for playlists, parses them and copying the tunes to the sync directory.
What this means is that I can right-click on any MusicBee playlist and "export as external playlist". That's all. The phone automatically sync the directory down every hour. I installed a Media Refresh app (there are dozens) to force the Android to see the new tracks, but it's rarely required. When I want to quickly sync and go, I manually kick off the sync from the.
That's just one way of doing it. On Windows you could install freeSSHd or a free FTP app on your Windows box and get an Android app to sync from them. The only bit you'll have to figure out is how to parse the playlist and dump the relevant files into your sync dir. Shouldn't bee too hard. You could do it with VBscript, python or good 'ole batch files. If you don't want to get your hands dirty, just select a bunch of tunes in the library and "Send To > Folder (copy)" and use one of these apps to sync from PC > Android:
https://play.google.com/store/apps/details?id=org.pcfilesync&hl=enhttps://play.google.com/store/apps/details?id=com.appricoo.android.tools.wifisyncr