But then, why not just use an ESP32 which can replace the Pi entirely in the proposed setup. ;-) I would have an ESP32 impersonate the MAC address of the serve

But then, why not just use an ESP32 which can replace the Pi entirely in the proposed setup. ;-) I would have an ESP32 impersonate the MAC address of the server passively (ie. only in the Wi-Fi association), then “push the wake button” if it found traffic that is allowed to wake the server. A wake-up firewall, if you will.