How do I transfer the music I ripped from cds I own to a new PC with iTunes?

Question

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, my co-worker has 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.
Do you guys have any thoughts on this dilemma? Would home sharing work better on this?
The iTunes version on both his computers is the same.  He is running Windows 7 on his new machine, and Windows XP on his old machine.

Answer 1

I don't know Windows, so all I can suggest is how one moves the iTunes folder to another machine via an external drive. Now, if he added tracks but did not have them stored into the iTunes library then they are stored elsewhere on the old computer or he's just going to have to re-rip them from the CD. BTW, if he rips them using iTunes, then they should not require any conversion. iTunes rips as MP3s. They shouldn't require any conversion.