Over in the announcement forum in the prop shield thread, Frank B posted a utility to download to/from the Teensy Propshield's flash memory. It may be all you need to do is make some modifications for your CS pin, etc. https://forum.pjrc.com/threads/33328-Prop-Shield-Beta-Test/page12.
Of course, it would be more useful if it could work automatically, and the Teensy could emulate a USB removable drive or a MTP device.
@frank b
perhaps adapt the code to work like this instructable? http://www.instructables.com/id/How-to-Design-with-Discrete-SPI-Flash-Memory/?ALLSTEPS
it allows one to program a spi flash over the serial
This works on windows for sorting by name: teensytransfer.exe -l | sort /+8
With the sizes left justified I cannot sort by file size, this would be a problem elsewhere I assume as well unless they are left side blank padded (to 7 characters if limited to <10MB).