Okay so I've already done some research on this and I seem to have an intersection of a few problems.
I have a drive /mnt/md0 that is a Raid1 3TB NTFS drive. My OS is 18.04.1 and is running off a separate SSD.
When I first right clicked on a folder in Nautilus it said "send to trash" and then when I did it would give me an error message saying it couldn't find the Trash folder. I did some research and found this answer: https://unix.stackexchange.com/questions/384237/cannot-delete-into-trash/384491#384491
So I followed these instructions to make a trash directory on my Archive drive.
sudo mkdir -p /mnt/md0/.Trash-1000/{expunged,files,info}
sudo chown -R $USER /mnt/md0/.Trash-1000
This made a folder with the required sub folders etc.
Now when I right click it doesn't say "send to trash" it just says "delete permanently". I want to be able to send it to the trash. So I did more research and I found that the issue was that the folder did not have the proper permissions. I thought it did because I chowned it in the second command but when I locked at a folder inside I could see that only root has ownership and permission. I tried again, and it didn't work. So I tried via sudo nautilus and it would flick right back to root, as described in this issue someone else posted: Permissions fail to change, even using sudo nautilus
Apparently this has something to do with the filesystem being NTFS. I chmod 775 /mnt/md0 aaaaand.... it changed the permissions! Now everyone can write and delete files. BUT delete permanently is still the only option.
What should I do? I guess I could give everyone read, write, and execute privileges but that seems risky. This archive will hold a lot of important sentimental backups for photos and stuff and I'm mounting into a cloud server and I don't want to expose it to unnecessary risks. Any suggestions?
This issue ended up resolving itself once I rebooted the machine.