Been playing with this for few moments and it looks like it is permissions and GroupFolder app.
To give you a little explanation, that’s what seems to be wrong.
I have a number of GroupFolders, one of which is called Templates.
My user belongs to a group that has full control (Write,Share,Delete) and same group has “Advanced Permissions” on that folder too.
The Advanced settings allow for self-imposed denial of access to Write&Delete within the folder (this is to allow only intentional interventions in the folder).
Now, if I undo the “Advanced Permissions” and delete a file/folder from within the Templates it will go in to the Trash and at this stage I can empty the trash too.
However, if I reapply the “Advanced Permissions” while the deleted file/folder is still in the trash it will get stuck and you can’t restore or delete it.
And now an interesting behaviour of the trash bin; If I attempt to restore a file from the trash after again changing “Advanced Permissions” to allow all, the file will go back to the Templates folder and will disappear without a trace (shows up for literarily a second and then gets deleted without going to the trash).
I think I’ll report that to the GroupFolder app issues 
Cheerio!