Strawberry 1.0.4 on Fedora 35
256GB FAT32 Samsung USB Flash Drive

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.

@jonas
Without the playlist the issue does not occur.
With the playlist it stops responding.
This also happens when loading the playlist on a clean start.

The setup:
Laptop with MinGW-W64 1.0.2 Strawberry installed.
Library on network drive, k:\music configured on Strawberry.
Playlist with 9.5k songs saved from previous use.
The issue:
Open Strawberry
Click anything, the first thing works.
Next click Strawberry goes unresponsive and uses 30% CPU
Must kill Strawberry in Task Manager.

I run Strawberry on linux as well and have only had a couple crashes, on this W10 laptop it's unusable. On a W10 desktop with a local library, it's been stable. Both were installed using the same installer file.
I've tried the other build and found Strawberry started and quit before ever showing a window.
This setup is identical to how it was setup for Clementine and I never had an issue when Clementine was used.

Being able to analyze with a tool similar to spek would be extremely useful when comparing tracks. It allows a quick visual comparison of tracks.
Why not just use spek? The spek project has been dormant for a few years now, I fear it may never get updated to be available on newer distributions.