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Did you drag the songs you wanted directly from the iHP and then save the playlist directly to the iHP? should be no problems when done that way.
If you dragged the songs from one drive and save the playlist on a different drive it won't work with the iHP because the filenames in the playlist will point directly to the drive & folder(s) where the mp3s exist rather than just the folder(s), open up the .m3u in notepad to see if there are any drive letters in the paths for the filenames - there shouldn't be any.
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