[georgekin]

To chime in on my workflow here, I used to be a heavy user of windows media player, until streaming became big and I bought into the Zune system - for which the software was incredible.

You could download media from the online library and it'd count as part of your local library, and you could create auto playlists that filtered all of your music (streaming and local) into those playlists. Then, you'd just auto-sync those to your devices.

This method isn't possible on any service anymore, and I believe it's because of increasingly more restrictive licensing. The closest I've found, and what I use today is google music. I upload all of my local content to them, and then mark songs that I 'like' as liked. GMusic has an autoplaylist of all my likes that I then sync to all my devices, including my car which has an android stereo.

I encourage everyone to step outside the Apple/Spotify walled gardens every now and then and resurvey the offerings - iTunes is just such an awful bit of software that it makes their service a non-starter for me. GMusic has a great mobile and web client, with download support which is all I need.