Hey Audiosavant et al.,
here's my 2 cents worth. Hope it helps!
http://www.computeraudiophile.com/category/Equipment/Music-Serversinfo about music servers if you decide to change your setup from a DIY server
https://www.hdtracks.com/index.phpgood source for hi res tracks - the only thing I dislike is that I don't get a physical copy of the cd/vinyl. =(
http://www.exactaudiocopy.de/aka EAC and a free flac ripper for windows - this is what I use for ripping my cds and essential software imo.
http://tmkk.pv.land.to/xld/index_e.html since you're using a Mac, XLD is the EAC (above) equivalent. If you want a concise setup guide please let me know and I'll email you the instructions. All audiophile level ripping should be done this way cause it'll save you close to 20% in terms of hard disk space and it's exactly the same quality as .wav or .aiff formats. With 5000+ cds that's roughly 750Gbs! Yikes! (I'm actually quite envious to tell you the truth)
http://www.dbpoweramp.com/alternative, but not free, flac ripper for windows
http://www.foobar2000.org/free music player/organizer for Windows - really, really recommend this for windows based computers
With regards to iTunes - if you download their music, it's in AAC format which is why the sound's sooo bad. It's not the iTunes player per se. I hate that organizer by the way. Much prefer foobar cause it's pretty minimalist and much more customizable if you want it to be.
[b7]fLuid
p.s. I'm about to post my audio setup, and I'd like to get some feedback. I think you might see why I prefer the idea/option of a Home Audio Personal Computer (HAPC) setup to that of a dedicated media server.
