I was able to swap with a buddy of mine, his Drobo FS for my Drobo S. I'm going to try and setup SMB shares and tie a \\drobo\nextcloud share to my data directory on the Nextcloud server and see if that takes the cake. I hope so. It should, but stay tuned for either success or more brain achy rants. I have higher hopes this time around though (kind of have to with last chances).

Drobo FS

Edit (4/22): Okay, so there have been pros and cons to this configuration. The Nextcloud portion works fantastic, I've had no qualms with my data\ directory being a symbolic link to \media\Nextcloud\ => \\192.0.2.1\nextcloud\. My issue has been more poised at my attempt at a Crashplan setup on the same server. I've had problems where the Ubuntu server loses the connection to the Drobo and...well...Crashplan doesn't realize this. It continues to backup data to the Drobo's mount point directory, thus filling up my drive to the point where I have 0 bytes of free space and to the point where a shell session has no resources to do tab completion. I end up umount-ing to make sure the drive really isn't connected, turning off the NAS just to be doubly sure (it is just me so that's fine), rm -rf-ing the directory to free up space and then re-mount-ing the share. I've since dropped the Crashplan setup on that server and stripped it to just being a web server since I've received my R710. I now have Crashplan running on a Windows VM on that ESXi box.