How did you delete the programmes from startup?
I don’t know anything about iTunes, i had a nano player once, but i got rid and got an mp3 player instead. Dou you carry your music on an iTunes player to play at venues? can u not keep music on an external hard drive? Sometimes converting from wmp to iTunes can make the music sound weird.
I have at times converted tunes from wav to wmp and has problems. I recently converted 85 Gig to wmp and all came out ok, maybe it's the bitrate.