I have a headless raspberry pi with a Schitt DAC via USB. I have a server (aka old PC with Linux) with terabytes of flac files, raspi mounts via NFS. Raspi has MPD (music player daemon) running. My laptop, phone, and ipad have MPC clients for select playlist, etc. i like it, the rest of my family doesn’t use it... they just play CD’s.
For the car I have traditionally burned CD’s. I just bought a new car without a CD player, I had no idea it was like that. Having only lossy music bugs the hell out of me. I’m thinking of doing the above in the car, with the added challenge of intermittent power.