The flaw is in the iptables implementation.
IPSEC originally uses UDP port P500 and ESP to establish a tunnel. unfortunately the current iptables version implemented in pfsense is not aware of ESP packets and cannot NAT them. as a result only one connection can utilize them.
once pfsense supports NAT-T your problem will be solved as it encapsulated the ESP packets in a UDP packet and routes them on port 4500.