Interesting. I am heading towards iTunes eventually. (Time to dump the 5 CD Megachangers) If I eventually go this route then I will need room modal correction for the bass signals - so I anticipate I will need a pro quality digital Paremetric EQ plug-in for iTunes (I like to be able to set frequency and Q as well as depth of notch filters precisely). Does one exist? Or is Amarra it?
FWIW: I ran tests recently with serving lossless from a wireless NAS 1 TB HDD to iTunes and played wirelessly via an Airport express with Toslink to a Benchmark DAC1. Extensive testing (flicking between optical sources with a remote from listening chair) has convinced me that there is no audible sound difference (to me) between a CD Toslink to DAC1 and the same CD burned (with error correction set to on) into iTunes and played lossless via a Airport Express toslink to DAC1.
Of course, I did not try a magic green marker on the CD's and my toslink cables were different in both type and length too - so my tests are probably invalidated for most folks with golden ears.