Hi Cockeye,

It sounds like you will want to re-rip your CDs to get the most out of
your Squeezebox.  The good news is that you will only need to RIP each
CD once.  Ideally this will be into a lossless format.  Once you've got
good rips in a lossless format you can always convert them to a
different lossless format with no loss of quality; and/or downconvert
them to a lossy format such as MP3 or AAC.

Take a look at this thread which describes an example ripping process
very similar to the one I use.  
http://forums.slimdevices.com/showthread.php?t=57787

Personally I choose FLAC which the Squeezebox handles natively.

Apple Lossless is perfectly acceptable although I think it's less
poplular here as it's use is a bit more restrictive.  It has the
advantage of working with iTunes; but you're still probably going to
need to downconvert the files to a lossy format (MP3, AAC) to put onto
an iPhone or other music player.

As for iTunes ratings; take a look at the Trackstat plugin by erland
http://wiki.slimdevices.com/index.php/TrackStat_plugin

Regards

Peter


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