You said you added the Tailscale network, but how wide did you go? By default when you load the plugin and activate the interface, it just gives its own IP as the network (/32). If you added that, then only traffic with that specific origin will hit your route. It’s crazy, but for my firewall rules (not routing) to work, I had to define the network as a 100.0.0.0/8, which is gigantic. You may have to do that with the route as you can’t otherwise set the gateway on the interface as it’s not hosting the DHCP server.
It might be the camera angle, but those faces might be throwing off the miters. If you’re aiming for perfect miters, starting with planed reference surfaces is a must. The alternative is what was mentioned above: cut proud and sneak up on it.