Pihole blocking internet unless pi is restarted.

Did you check network connectivety on the Pi when connecting KVM (Keyboard Video Mouse)?
Are you able to login on console?

Also check for below:

https://www.raspberrypi.com/documentation/computers/raspberry-pi.html#power-supply-warnings

Could search all of the systemd journals with below for "under-voltage" messages:

sudo journalctl --full --no-hostname --pager-end --grep voltage