My considered opinion is that Apple offers very poor choices for running a 
dedicated media server.  You need iTunes open and running on your dedicated 
machine, and you also need remote control over that machine, or keyboard access 
to it, to update the iTunes database any ways besides adding content (which can 
be done over the network using iTunes’ "Automatically Add to iTunes” folder).  
This might be feasible if you are one person and you can be relied upon to 
perform the management, but there’s no hope of centralisation for multiple 
users, you can’t download to iOS directly from the server, and unless you know 
of a remote-control tool for Mac it’s going to be a pain anyway.  It’s not 
going to be the dream experience you’re hoping for, I’m afraid.  My resolution 
has been to avoid DRM content as much as possible (which, naturally, is 
actually quite hard) and then store the media on a NAS, using permissions to 
handle it on the file server and having people manually copy over what they 
need into their own libraries.  I have an iTunes Match subscription which means 
I can put into the cloud whatever collections of music or audiobooks I want 
access to.  Then Apple TV streams wherever possible directly from Apple any 
content I’ve bought or matched with iTunes Match, and only if I need something 
on my computer do I fire up and minimise iTunes.  It’s a pain, really, but it 
works.

I have yet to try Plex, but I know it handles music.  Perhaps if it provides 
better remote management, a Plex server would make a lot of sense.  And it’ll 
run on the cheapest box, or on platforms other than OS X.  When I’ve a mind, 
and if I don’t begrudge them the money, I’ll take a look.  Plex doesn’t need a 
cloud to work, unlike Apple’s services.

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