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OK, I'm shootin' in the dark here, too, but what the heck..
I've got a '13 FR-S w/ the stock base head unit, too, and it plays back my entire flash drive without any problem, as you mentioned.
When you say that you've got your files on the drive in a particular order, that isn't really true; the files are just data scattered around the drive however your computer thought was the most effective way to save it at that time. The files and folders are indexed in a certain way and, on your computer, you can display them in various orders (by file/folder name, by date, by size, blah blah). On mine, I save the tracks from each CD in a separate folder named the same as the CD's name, then I save THAT w/in a folder named by artist. The HU in my 2013 plays all the tracks in order, artist by artist.
If your HU won't do that, have you tried putting your flash drive in your computer, then dragging all of your individual track files into one huge directory? It might make finding a particular file difficult/impossible in the future, but it'd probably accomplish your goal of non-stop playback. On the other hand, if the id3 tags for artist/track/album are still in place, your HU might STILL be able to access things by album, even though you don't have them saved that way on your drive.
Just an idea... have no idea if it'd work.
Barry
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