I use Mac as well. A few suggestions, and you may not like one: I've done quite a bit of experimenting and listening comparisons. I am only suggesting this because you stated you want to squeeze out every bit of musical pleasure for those zeros and ones. You may want to try ripping a few files to AIFF using the latest version of iTunes and see if it makes any difference to your ears and on your system. Yes, I know AL is lossless. I was particularly struck in differences between the sound of a file ripped in AL compared to the same file ripped using EAC (a PC-only software). You can find various debate and discussion on this topic on this and other sites. The only reasonable explanation I've heard for it is that the algorithms used to compress and decompress AL may account for differences in the files sound. Reportedly the latest version of iTunes addresses this to some extent, but this is hearsay and I've not actually compared rips on the newer version to those from the previous version. It may be worth trying yourself if you want to determine what works for you. Results will largely be dependent upon how revealing your system is, as well as your personal discrimination. Additionally, I've always preferred coax to optical, but the best optical I've tried has been a Wireworld Supernova (I think it is only a version 3). Perhaps I'll have to revisit that. Again, whatever works best for you. The best digital I've heard via computer files is far and away via the Modwright Transporter, which is a wireless server as well as a DAC (disclaimer: Modwright is a client - I do their photography and graphic design). I recently did comparisons with a friend to Empirical's Pace Car and Empirical modded Northstar DAC, as well as an Electrocompaniet EMC1-UP player and MHDT Havana DAC. The MW TP bested all in numerous blind tests we each did, unanimously and without hesitation. This was in a very revealing system using a wide variety of music. There are of course many other options to compare it to, but that's what I'd recommend given my experience. The other one I'd be curious to audition is the Berkley Alpha DAC. I have not heard it though.