Since you have an IPod, you should use ITunes do do your music transfers. I-Tunes can be downloaded at
www.itunes.com ^.^ it has a feature built in that will let you connect directly to your IPod, and transfer music and files and stuff to it
*Phoebe hates musicmatch with a passion cuz it uses up a lotta resources, keeps coming up with updates that you have to pay for, and takes a long time to load up*
But ya ^.^ I'm sure if you use ITunes, it should transfer no problem, because Apple makes sure they get stuff done right the first time
