The CD and line level inputs should be identical electrically.  (CD is a
line level source).

In your setup, theoretically the best sound quality will be obtained
with the squeezebox volume set to max.  Once you reduce the volume by
6dB or so, you will start to lose dynamic range coming out of your DAC.
However, your amp and speakers dynamic range will also reduce with
reduced volume, which will mask this effect.

Given "The amp actually has separate volume control for both left and
right, so it's kind of a pain in the ass to volume-match correctly"

I would adjust the amp volume once so that maximum squeezebox volume is
equal to maximum normal listening volume, and then use the squeezebox to
adjust volume on a day to day basis.  If you plan to have a party or
something, then you can re-adjust the volume on your amp for the
occaision.


-- 
bludragon
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