Very weird behavior after update. Losing connection every 5-10 minutes, gain it back for a few minutes, lose it again, for hours now.

Check the systemd journals with below (also read the follow ups):

Also you could try a higher spec AC adapter for power to see if things improve.
Or another USB cable to power the Pi.
Plus disconnect all USB devices connected to the Pi.
See below:

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

I still run Pi-hole on a:

$ cat /proc/device-tree/model
Raspberry Pi Model B Rev 1