1. Format flash drive to FAT32.

2. Mount flash drive in Strawberry.

3. Highlight all tracks on playlist with 9496 tracks.

4. Copy to device.
   Naming options;
   %albumartist/%album/%title.%extension
   Remove problematic characters from filenames
   Restrict to characters allowed on FAT filesystems
   Restrict characters to ASCII
   Allow extended ASCII characters
   Example Image showing the settings.
   

5. Click OK

6. Process completes, no error message is shown.

7. Strawberry reports 9391 songs exist on flash drive.

Changing the copy settings has made no difference.
I went through all my music and translated all titles so that all characters are supported by FAT32 to be sure that wasn't the issue.