Are you sending the photo from your library on your computer to your Message account also on your computer? I'm able to do that so try the following: boot into Safe Mode (How to use safe mode on your Mac - Apple Support) by booting with the Shift key held down and check there to see if the problem persists. Reboot normally and test again.
NOTE: Safe Mode boot can take up to 10 minutes as it's doing the following;
• Verifies your startup disk and attempts to repair directory issues, if needed
• Loads only required kernel extensions (prevents 3rd party extensions from loading)
• Prevents Startup Items and Login Items from opening automatically
• Disables user-installed fonts
• Deletes font caches, kernel cache, and other system cache files