Allow me to complicate the story.
He had a computer, he also had a wife. He no longer has a wife, and he only had 45 minutes of access to the computer.
He did use iTunes (though the account was hers), and many of the songs were purchased from there. I've managed to talk him out of going that way again, but he doesn't want to lose any of his music. I've found .mp3 and .wma files so far, but I haven't gone through all the hundreds of folders yet.
I just want to make sure that everything will play on anything. The only sure thing I know of is MP3.