This question is for researchers who have and use iPod extensively
with a Windows machine.

1.  I just got my iPod.  I have an extensive library already in
MusciMatch.  However, for now I'm going to the trouble of re-ripping
from CDs.  Unfortunately iTunes doesn't seem to recognize and label
tracks as well as MusicMatch.  Are there any workarounds to this or is
there something I'm not doing right?  Otherwise I'm going to have to
painfully enter in track names for tracks on CDs that iTunes doesn't
recognize!

Thanks.

You must have many obscure CDs.  My collection which is eclectic (OK,
heavy on 80s music, alot of it almost 20 years old.), has not had this
problem.

You can try downloading iTunes 4.5, the latest version of Apple's
jukebox software, from here:
http://www.apple.com/itunes/download/

 - supermacman-ga

this is so basic
 all you want ot do is play you song that you riped in musicmatch on
your ipod. all you have ot do is copy them over
and as long as they have the the right mp3 tags if you go on the
browse option on your ipos meun you'll be able to play them

To: Bobak-ga

I should have mentioned that I am re-ripping the CDs to take advantage
of the better compression algorithm on the iTunes/iPod platform (AAC
instead of MP3).