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Finally figured it out, but it's not pretty. I tried a bunch of different ways to get a playlist on a USB stick (windows media player, itunes, mediamonkey, iExplorer) and no matter what I did it always played in alphabetical order. I attempted to add a prefix (e.g., 1a, 1b, 1c) to the file name, but it made no difference. I discovered that you can do this, but it has to be under properties for the file and is needed to be done on the title, not the filename.
Too much work when you're talking thousands of songs. :-(
~Jim
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