@doktornotor:
Does this file exist? /usr/local/etc/ssl/cert.pem
Yes, it exists. The problem ended up being the networking+hypervisor setup. We had LRO enabled and it was causing issues on the pfSense guest. After disabling it ALL packets were properly hitting the pfSense guest.
Running in to other quarks which I don't quite understand why they were designed this way. After establishing an IPSec tunnel I'm unable to traverse over that tunnel from the shell of the pfsense box - but if I add a route (which then causes a routing loop), it does. An example would be to setup an OpenVPN server and have it authenticate against an LDAP server - pfSense can't reach the LDAP server if it's over the IPSec tunnel. Quick fix to that was adding a route. Doesn't seem like the right thing to do.
pfSense in this case is used to extend the network to a new location over an IPSec tunnel as well as act as a VPN server at that new location.