For what it's worth, when I had to solve the same problem that Roger is tackling, I ended up punting to the cloud, uploading everything to Google Music ...
That's one nice thing about Plex... If you configure things properly, you can access your media stored on your plex server via the public internet. So the benefits of cloud without needing to upload everything.
When everything is set up right, it's transparent: Fire up the Plex app on the phone and get the same content regardless of whether you're on the same LAN as your NAS or on the internet.
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