I can't actually delete photos from Lightroom on my Mac system. I simply get an OS message that says 'Unable to move file to trash can'. I know the difference between 'delete' and 'remove', have read many discussions threads on the topic of deleting photos and know to attempt the delete from the grid view in their original folder. ...I used to be able to do this but for some reason it no longer works. i'm quickly reaching my disc storage limit and have to get an answer soon.
How much free disk space do you have? I'm wondering if perhaps you are so full that there isn't even room to put them in the trash.
Also could be permissions. Read this article. Repairing permissions: What you need to know | Macworld
I also use disk warrior for this type of issue. see DiskWarrior 5 - The Disk Utility for Mac Disk Repair, Mac Directory Repair, Mac Disk Recovery, Mac Data Recovery
@75 gig. Btw, I can delete from this folder via the Finder app.