@weyon668 here is what I would suggest you do then.
Your stuff your trying to get to is on your lan network? You can ping your pfsense lan IP.. Ok now sniff on your lan interface for icmp and your destination IP.. Do you see the ping go on?
If so and you get no answer, then the device your pinging is not answering, or he is sending the answer to something other than pfsense..
Here I connected to my openvpn on my phone via a cell connection - and pinging my nas..
vpn.jpg
That 10.0.8.2 is my phone, you can see it sends on the ping request, and in my setup my nas is answering.. Are you not seeing the ech request go out towards your devices IP your trying to ping?