It seems like updating Ubuntu LTS releases always has a few unexpected surprises.
I did not seen meaningful solutions on Google, so maybe this will help someone.
For booting to a black screen.
It was related to the GPU drivers. I was using x.org’s nvidia drivers and purging them and reinstalling fixed it. Of course since you’re at a a black screen you will need to ssh in.
# To see available drivers
$ sudo ubuntu-drivers devices
#Purge old drivers
$sudo apt-get autoremove –purge nvidia
#Install new drivers
sudo apt install xserver-xorg-video-nouveau
sudo reboot
To fix the VNC:
Either go to a terminal and disable wayland. I never had to do this prior, but apparently it’s a common issue.
$ cd /etc/gdm3
$ sudo nano custom.cnf
Remove the # from WaylandEnable=false
$sudo reboot