obviously that's not normal use case for a normal person and not being able to do that wouldn't even be in anyone's wildest radar.
I dont use Apple Music or iTunes anymore, it has caused too many headaches.
But i DO use PlexAmp. And it works great, works with FLAC, will transcode, and allows you to selectively cache things.
Its not perfect. There are hiccups with transitioning to Carplay for example. But in general, if not for PlexAmp, i likely would have ditched iPhones after having them since roughly the 3gs (with a few google/Android phones smattered in between, namely the Nexus One and Galazy Nexus).
How is Windows easier in this regard? Managing Windows clients requires a whole cluster of Microsoft services, no?
For basics you only need a one machine with Active Directory role installed. Everything else depends on the needs.
Is there something specific you found unacceptable?