I finally managed to set PermitRootLogin to yes in openssh_config by creating a copy of the openssh startup script and modifying it so it wouldn't overwrite openssh_config every time the service starts. I then modified bootlocal.sh so it would start my script instead of the usual one, backed everything up, restarted and I could finally log in as root.
Something strange is happening however. Even if I use the root username and password to log in via SSH, once I'm connected I get the tc@box prompt and don't have any of the root privileges. So it would seem I'm effectively logged in as tc even though I use root's credentials...