Tunnelling/VPN question

So, I am helping troubleshoot a piece of a network, and I have run into something that seems odd.

There are 2 tunnels in the setup. Devices at the end of the tunnel cannot communicate across the Layer 3 Cisco switch to stuff on the other side. They appear to be getting a good connection to the switch, though

The tunnels go out FA0/1, using the IP address assigned to the port as the source. The IP address of the port is in the same subnet as the WAN link.

interface Tunnel0

ip address 10.44.2.2 255.255.255.252

ip nat inside

ip virtual reassembly in

tunnel source 50.208.230.57/29

tunnel destination 66.174.16.250
tunnel vrf xxx

So, Fa0/1 50.208.230.57/29
G0/1 50.208.230.58/29

There is a route in the routing table of 50.208.230.56/29 going out the G0/1 port.

I have 2 questions:
1. I have tried using Packet Tracer to recreate the situation, but I can't find a switch or router in there that will let me use an IP address as the source of a tunnel. Is there one?
2. Would this setup cause an issue with traffic going across the tunnels?