Pihole DHCP is unreliable and intermittent

Try run a tcpdump.
EDIT: Run below if not installed:

sudo apt install tcpdump

Example for how below:

Notice below lines in the dump (DORA):

            DHCP-Message Option 53, length 1: Discover

            DHCP-Message Option 53, length 1: Offer

            DHCP-Message Option 53, length 1: Request

            DHCP-Message Option 53, length 1: ACK

You could also install Wireshark on the Windows PC to inspect if you have a full DORA exchange.

EDIT: On the Windows PC you'd have to run below first:

ipconfig /release

And if you run below afterwards, you'd expect to see a full DORA:

ipconfig /renew

I had to lookup how to do it with Wireshark.
You can use the same expression as with tcpdump in the Wireshark filter (dont forget to select an interface like I did):

(udp port 67 or udp port 68) and ether host XX:XX:XX:XX:XX:XX

Replacing XX:XX:XX:XX:XX:XX above with the MAC address of the Windows ethernet NIC.
You can see that one if run below:

ipconfig /all

So you dont see any of the other network clients broadcasting for DHCP.