Here is the nat table in the DDwrt. And just for clarification, I AM actually able to connect to the webGUI, it's just that I usually don't get and styling (although sometimes I do). Only sometimes I cannot connect at all.
All phones register with the correct IP to the asterisk server.
What would be odd to me is if the tunnel is set up and happy, why would a NAT cause pfsense to block the connection at the VPN level (it's blocking the VPN packets, rather than the actual traffic). In other words, right at the moment the call is placed, pfsense blocks all connections from the remote site's public IP address. And, for what it's worth, I do not observe this behavior with anything else coming over the VPN. Even when I have the issue with the webGUI, nothing get's blocked (at least on the pfsense side).
Chain PREROUTING (policy ACCEPT 1162 packets, 304K bytes)
pkts bytes target prot opt in out source destination
4 244 DNAT icmp – * * 0.0.0.0/0 [public_IP] to:10.51.2.1
60 8983 TRIGGER 0 – * * 0.0.0.0/0 [public_IP] TRIGGER type:dnat match:0 relate:0
Chain POSTROUTING (policy ACCEPT 59 packets, 5237 bytes)
pkts bytes target prot opt in out source destination
223 12561 SNAT 0 – * vlan2 0.0.0.0/0 0.0.0.0/0 to:[public_IP]
0 0 RETURN 0 – * br0 0.0.0.0/0 0.0.0.0/0 PKTTYPE = broadcast
Chain OUTPUT (policy ACCEPT 61 packets, 4331 bytes)
pkts bytes target prot opt in out source destination