Strawberry 1.0.4 on Fedora 35
256GB FAT32 Samsung USB Flash Drive
Format flash drive to FAT32.
Mount flash drive in Strawberry.
Highlight all tracks on playlist with 9496 tracks.
Copy to device.
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.
Process completes, no error message is shown.
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.