Please let us know if this is still occurring with 22.214.171.1241, and if yes, send in a debug log.
p.s. is the drive using the d_wmdm sync plugin or the USB Mass Storage plugin (you can check at Tools > Options > Portable/Audio Devices).
Rusty - it's using the USB Mass Storage plugin; just downloaded 1501 & am trying now. I isolated a few errors that I may have caused (by using separate directories for music "waiting" for review & music that "has been" reviewed. I'll let you know how the synch goes.
One other question, though... if you initially drop files into one sub-directory, then update the tags, etc., and move it to another sub-directory (within the same tree folder), will the "Add/Rescan files to the library" make the changes for you, or is there some manual step that must be accomplished prior to the synch?