Bartender,

Is therr some FREE software I can get that will search my whole
HDD for any file paths which are too long?

You first need to figure out what the maximum size of the path + filename is
for your USB stick. After that a bit of VB- or JavaScript will do.

Google the web for iterating a folder tree using either of the above script
languages, and you most likely will find multiple examples. After that
its just comparing the length of the returned full filenames (drive + path +
filename) to whatever limit you want.

Regards,
Rudy Wieser