@brannenj that screams firewall on the device..
Simple test.. from your wireless vlan ping the IP of the server, when you sniff on pfsense interface on the server interface.. Do you see pfsense send on the ping? If so - and no response then there is something on that device not answering the ping, ie firewall..
Here... pinging another on one of my vlans 192.168.2.50, from my 192.168.9.100 device.. While sniffing on the interface the 2.50 device is on..
request.jpg
If you only see the request, then pfsense sent on the traffic, but the device your pinging is not answering.
If you don't even see the ping requests go out, then pfsense never saw it? Your policy routing traffic, or your rules are not actually any any.. If you dont even see the requests go out on the interface for the server, validate the traffic gets there by sniffing on the pfsense wifi network interface.