Export itunes to USB? Need Help

in iPod + iTunes + AppleTV edited January 2014
Somebody, please help? Why is this so difficult.

I read under one internet search that you need to copy the files first into a finder:folder and then copy from finder:folder to USB? This seems to work, but not how I am intending. All of my music files have a number (i.e. 03) in front of them and most files do not maintain the album artwork (i.e. <30%).

Can anyone explain what I am seeing above and how to do this better. I am ok with keeping the *.m4a extension, as my Ford SYNC will play those files.
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