Issues with iTunes on PC. o_O!

[trapspringer]

Greetings y'all.

Some one I work with uses iTunes, and he wants to transfer all of his music from his old computer to his new computer. I went to the apple website trying to find answers. They have some pretty decent tutorials on how to transfer your music from one PC to another PC.

However, here's the curve ball, They have much music that they ripped from CDs. Whenever I tried some of the methods detailed on those tutorials they would simply not transfer the ripped music, all of which he legitimately purchased.

One of the methods details simply going to the folder that iTunes stores the music and copying it to an external then copy pasting it on to the other computer. When I tried this it not only did not copy the ripped music, it deleted it off of the external. Only the music which he purchased on the Apple iTunes store transferred over successfully.

He still has his old computer and won't get rid of it until we know for certain that his music is safely on his new computer. I have informed him that going forward he should not use iTunes to rip his cds, rather he should possibly use WMP and set it to rip cds to mp3s at higher than 192 kbps rather than m4as. Yes I know there are better programs out there for ripping CDs, and on to different formats, but I'm trying to keep it easiest for a layman.

Do you guys have any thoughts on this dilema? Would home sharing work better on this?