Hello, I'm not a networking expert but will try to give as much information as possible.
I'm running PiHole on a Raspberry Pi 1 Model B with DietPi.
My network begins with my ISP router, which I'm afraid I'm not allowed to change. It does come with some settings, but won't allow me to configure a dedicated DNS. I have therefore disabled the DHCP in the router settings and enabled the DHCP server in the pihole configuration, following the manual.
I have a second router wired to my ISP router, located in a different area. It's emitting a wifi and set to bridge all traffic to the ISP router. So on my ISP router, all clients coming from this connection look wired. For all of this, pihole works as I'd expect.
My ISP is also emitting a WiFi. When I try to connect to it, it looks like the client is not receiving an IP address and therefore, no network access is possible (tried with Android & MacOS). I also tried manually assigning an IP to the client, but network access remains unavailable. I remember from my university days that DHCP over WiFi is not as straight-forward as ethernet, but haven't found any further help on the internet so far.
Of course, I can connect with both clients using the AP WiFi and they will connect just fine. I assume this is because to my ISP router, they now look like a wired connection.
Here's a crude image of my network topology to maybe understand the issue better. I'm also happy to post log outputs from my Mac, if there's any commands which might help in finding the cause.
Edit: In case it helps, I have some syslogs from my Linux notebook trying to connect. It looks like DHCP requests are timing out. I'm not sure why this would be, but I'm starting to think this is a problem with my wonderful ISP router instead of pi-hole.