tok20000 - you have xld and max for the mac. they are excellent rippers.
as for toslink, i like using coax when going from a quality cd player in to a dac. as for a music server, i isolate the computer from the audio room (from any room that is served from the server for that matter). i don't want a computer in my audio room. you have raid disks spinning, backup disks spinning, fan noises, etc..
so i use devices that allow me to stream the signal over ecat5 or wireless (audio rooms are wired using gige speed). to further isolate any noise from these devices, i use toslink into a jitter device. then i use coax into the dac. no noise, dead quiet.
even in my den where i use the music server, i don't go directly into the jitter device from the computer. i still route the signal over the net (5ft away).
using toslink in network devices that are hooked up to electricity and to the network, toslink is less susceptible to pick up any em or rf interference like you would with a copper cable. also, you might have to run a longer cable to your dac which toslink would be a better choice for longer runs.