You'll get quite a few opinions with this.

Personally I use a windows program called dbPowerAmp to both rip and
encode.  It is very good about getting accurate tags and encodes to
FLAC on the fly so by the time the CD ejects, the FLACs are encoded
already.  

Once I've ripped my FLACs, I then use dbPowerAmp's batch encode to
create mp3 versions of the files in a separate directly.  These I then
import into iTunes to use with my iPod.

dbPowerAmp, with tagging and mp3 support, does cost money (~$40 maybe? 
I forget).  Free software you can use are a combination of EAC to rip
you CDs (and encode to FLAC directly if you like) and foobar2000 to
create the mp3 files.  This will give you the same results, but may
require a little more tweaking to get things going efficiently and you
may have to intervene to fix up tags received from freedb.

If your existing iTunes files contain DRM, you can't use them with the
squeezebox.  If they do not, you should be able to play them directly
without encoding them to FLAC.  There is no advantage to converting a
lossy file to FLAC - the file will just be bigger with no improvement
in sound quality.


-- 
maggior

Rich
---------
Setup: 2 SB3s, 4 Booms, 1 Duet, 1 Receiver, 1 Touch, iPeng on iPod
Touch.  SuSE 11.0 Server running SqueezeBoxServer 7.5.0, MusicIP, and
SqueezeSlave.  
Current library stats: 34,767 songs, 2,776 albums, 505 artists.
http://www.last.fm/user/maggior
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