You rip a CD and it pretty much gets organized the same way iTunes does.
I don't like amount of scrolling you have to do to get to particular album in Itunes, but if you create "smart playlists" for each genre (like "genre IS Jazz") then Itunes displays whole page of thumbnails of all records in the genre - much easier to use.
As for the server - I use WiFi on Mac Mini to transfer data (on 5GHz band) to Airport Express, then by Toslink to Benchmark DAC3. I keep my computer ON all day placing it in the "SLEEP" mode at night. It wakes up instantly. Since I'm sending data (no timing) over Wi-Fi computer (playback program, speed, amount of memory) is not important. Same (other than conducted electrical noise) goes for Ethernet or async. USB.