Help me to understand why DHCP does not work

Yes. This are related to earlier question. Earlier I was trying on Rpi3 where even DHCP was not working.

Today, I tried on Rpi4b, where my Windows machine successfully gets IP from Pihole.

I put DHCP on 192.168.10.0/24 subnet instead of 10.102.132.0/24 because the later was given from my ISP.

I'm having hard time understating everything, perhaps you can simplify the questions for me? Oh and you can close the previous question (or merge this).

I would love to get some understanding on what is going wrong.