I'd say a good ripping solution + a decent DAC out would be the best way to go. A properly set-up EAC on Windows is probably the best option (which you can also use in a virtual machine in OS X like VMWare or Parallels). However, XLD (X Lossless Decoder) is a very good option natively on OS X, though not quite as solid as EAC.
From there, encoding to Apple Lossless and managing the tunes in iTunes is probably the best bet for you.
After that, it's about getting the audio out. Many speak very highly of the Apogee Duet Firewire DAC, but I have no personal experience with it myself. Clearly there are several folks here more experienced with that end of things, so... listen to them? :)
From there, encoding to Apple Lossless and managing the tunes in iTunes is probably the best bet for you.
After that, it's about getting the audio out. Many speak very highly of the Apogee Duet Firewire DAC, but I have no personal experience with it myself. Clearly there are several folks here more experienced with that end of things, so... listen to them? :)