Update:
This has been solved and can be closed.
@johnpoz:
Can you say hairpin, can you say /2 bandwidth, can you say pointless in such a scenario.. Because he wants to hide his public IP?? WTF???
Why not just host what ever he is doing at IP 1.1.1.1?? Use less bandwidth this way.. Clients get better response, No hokey/borked setup and they don't know about IP 2.2.2.2 ;) which seems is the goal.
Yes, this would be a hairpin. It would half the throughput, but the load on said link is negligible. I really don't feel like arguing semantics, so im just going to leave it at hairpinning works just fine in pfsense.
He's unable to host locally, and the ultimate goal was to allow web servers to be dynamically provisioned and accessed without requiring constant DNS changes.
While it's possible to nat the traffic, there were other constraints that would not be met doing this method. The answer was setting up a reverse proxy, which also adds the benefit of acting as an accelerator.