The HDMI output should give you a console output of the linux system startup processes. You can look for errors there. There’s also logs but I’m not sure which ones to tell you to look at.
You can also check over SSH when it gets stuck and see if you can still login/etc (is linux running?). If not, then its likely a linux system problem or perhaps power related(?). If things are running, but norns or orac are not starting, then journalctl -r can give you some info to see if there are errors. dmesg is also helpful to look for power related warnings (like Under-voltage detected!).
Then the following will show info/status for the norns processes:
systemctl status norns-matron.service
systemctl status norns-crone.service
systemctl status norns-jack.service
systemctl status norns-maiden.service
systemctl status norns-sclang.service
and then orac/sidekick
systemctl status orac.service
systemctl status sidekick.service