Hello Edward Franskevicz:
As shown in your information picture your board only has an MSD bootloader firmware (Mass Storage App):

What you need is either a Debug firmware or the combined MSD + Debug firmware.
Please carefully read all the next tutorial by colleague Erich Styger:
Illustrated Step-by-Step Instructions: Updating the Freescale Freedom Board Firmware | MCU on Eclips...
And about Windows 10, it indeed matters. You may need a Windows 7 machine to update the bootloader from version 1.09 to 1.11.
Best Regards!
Jorge Gonzalez
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