Cannot play AIFF files properly

For various reasons I need to have some music on my iPod classic stored and played as AIFF files (or WAV...just full sized files anyway). So far, I've been unable to get this to work properly. Certain songs don't play at all, one jams, and the iPod has crashed while playing another (its never done this using MP3s like normal, after 2 years of regular use).
A friend of mine has tried the same thing with an iPod classic, with the same results. Has anyone else tried this and experienced the same problem?

I have successfully copied audio CD's in the past. I have the preferences set for audio CD. Is there another place to set the file type? Does it matter what type of blank CD is used? This one is a RW. Ones I have done In the past were just recordable.

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