@Derelict Thank you. When I replied, I didn't have access to the device, but looking at it now, if I'm understanding everything correctly, I changed the Interface setting of the Pfsense Packet Capture from WAN to OPT, which is the the port the server is plugged into (as labeled on the device and afaik I have not changed the label anywhere in software). This yielded no traffic. However, when I check the LAN interface, I can see the expected traffic. So I guess that means it's making it past the firewall successfully but may or may not have a route to the right place.
As I noted in my OP, I did move the OPT interface to be on the same VLAN as the LAN interface (so I can access the server by direct local IP from my internal network - works fine). I am in the process of double checking those settings. Also still going over the Troubleshooting guide linked above.