Thanks for the comments. Like you, I have been spending a lot a lot of time lately ripping my CDs to .wav. I am using Exact Audio Copy.
Thanks for the suggestion regarding the external DAC kit. For now I am using the analog outputs on the Squeezebox. If I succeed in convincing my wife that we really do need 4-way speakers and a fancy amplifier then I'll probably try for the DAC as well. We'll see...
System edited: System edited: The Squeezebox arrived last week -- how did I ever live without this device? Very convenient. My amp is now hidden in the cabinet and I've put an orchid in its place.