Thought I'd post some notes about my journey which led me to Roon and Plex. I've always thought Apple's music products - while at the forefront of a lot of Apple marketing, have technically been lagging behind. It amazes me that a huge company with such vast resources, can't produce a mobile player that can support high bitrates of their own music format (ALAC). Everything is down sampled, or in some cases - end up disappearing into unreachable areas on the iPhone, where iTunes would play the file but the iPhone couldn't. I ended up buying a Fiio X5 (2nd gen) for portable listening, and for listening in our office in a comfy chair. This year we purchased a perpetual license for Plex, and started using it for our video - TV shows and Movies. There's a Plex client for AppleTV and the interface is quite nice. Drop downloaded files into a file share, they should up on our TV for viewing. I ended up losing my X5, likely leaving it in Los Angles on a recent trip. I decided to do some fresh research into what I could do, technology wise. We have a McIntosh C52, MC302, a REL sub, and some Vienna Acoustics speakers in the living room. In the office, I have an exasound e20, Auralic headphone amp, and Beyer T1 'phones. That's where I was plugging in my X5. After some heated discussion about having to run wires, having to run MORE computers at home, we landed on what's become a simple solution. We started using Plex for Music on our mobile devices. Our media computer (running the Plex server) was tasked with indexing our large iTunes library. Then the Plex iOS app was installed, and it made synching and playing music pretty easy on our phones. We stopped using iTunes at this point. Then I decided to try Roon. I got a Hifiberry Digi board for the Pi, so it had digital coax out (going to the DAC). I started the 14 day trial. Everything I'd heard about Roon turned out to be true. It's nice, it's fast, and it does everything I wanted. I can play music in the office's iMac and in the living room on the nice speakers (grouping outputs together), PLUS play something differing through the Pi to my headphone station. 48 hours into the Roon trial we've decided to purchase a perpetual license. It costs as much a nice media player with Micro SD cards, except our library can stay put. The remote is responsive enough that it's pretty much the same experience from the chair. So now we're using Plex to sync music to our phones, and using Roon for music at home. We can play anything, anywhere. And the Roon app reconnects so much faster than the iTunes remote app. Here's the Pi on top of the DAC. Here are some iPhone screenshots of the magic happening with Roon: EDIT: A few other notes: 1. Roon connects to Core much faster than Apple's Remote app. 2. Roon and Plex both do great things with metadata. They present our music library with lyrics, album covers, related artists -- and Roon can play similar music after an album is over. Just a lot more though into the experience. 3. Both Roon and Plex are watching our secondary music library location. So we can just drop new content in, both systems pick it up and index it.