Q: Can't Delete/Empty Files From My Trash

Hello obogans,

Thanks for that info and choosing the Apple Support Communities. I know how important deleting these files is to you! Based on what you stated, it sounds like you have tried some good troubleshooting steps already. Here is what I suggest you try next to resolve this:

1. Use Safe Mode to start up your Mac so that it performs certain checks, delete system cache files, verifies your startup disk, and attempts to repair directory issues if needed. Then try deleting these files again.

Try safe mode if your Mac doesn't finish starting up
Limited graphics performance in OS X recovery or safe mode

2. You can figure out if unexpected behavior is related to user file or setting by trying to reproduce the issue from another user account. This process includes creating a new user account, logging in to it, and testing for the issue.

How to test an issue in another user account on your Mac

Cheers!

Sounds like you have tried most of the troubleshooting for your situation, so you may need to contact AppleCare support as they have more tools and resources for your specific issue. This link will help you get in contact with AppleCare support:

Contact Apple Support

Have a great day!