Thanks guys for the continuing input. I'm inclined to keep going on transferring my CDs to PC with iTunes and Apple Lossless. Seems like the easiest path and hopfully retains highest quality source.
I'll then need to figure out optimum dac, connection (USB, Firewire, or wireless to Squeezebox followed by toslink to high-end dac, or wireless to Transporter and use as is, or output to seperate high end dac) and if/how I need to solve clock/jitter issues seperately. It seems like the Benchmark is a good option for to solve most issues, although I really really like the Duet remote (I may experiment with getting an iPhone which can be used as an iTunes remote too). Anyways, sooo many options - it would be easier if there were a consensus single best quality option, although it can be fun to waste hours reading and arguing about it too :-)