Hi Doug, I think the short story is that you're managing the service the wrong (old) way. Ubuntu moved to systemd as of 15.04. This should help: https://www.digitalocean.com/community/tutorials/systemd-essentials-working-...
sudo service tor restart sudo service tor status
These are now outdated commands, and so the results will not be what you expect, and the output of the latter will potentially be misleading. You need to use systemctl (check the above guide).
For all I can gather, Tor isn"t running. The odd thing is if I reboot my VPS by sudo shutdown -r now and do ps aux | grep tor there is tor running as a root user
It's being started by systemd on boot, as seen in the output of ps here:
root 435 0.0 0.5 44760 5716 ? Ss 19:40 0:00 /usr/bin/tor --defaults-torrc /usr/share/tor/tor-service-defaults-torrc -f /etc/tor/torrc --RunAsDaemon 0 --verify-config
That looks sane/typical to me, for what it's worth.
There are no files in/var/tor/log
Check in /var/log/syslog; I'm not sure why logs go there instead of /var/log/tor, but it may be another artifact of Ubuntu's switch to systemd.