I have tried heaps of different configurations, during which if I hit any address in the 192.168.100.0/24 it would just take me to the LUCI interface of OpenWRT. I have tried adding a static route in OpenWRT from the WAN interface to the LAN Gateway. I tried bridging the WAN and LAN interface. I tried making the WAN interface a LAN interface. I have the firewall rules as open as possible. I noticed when I add static routes in the UI, they do not show up with an 'ip route'.
Did you turn off masquerading on the WAN zone? And did you allow forwarding from WAN > LAN? Those are both important.
If those don't fix the issues, let's see your configuration...
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You do not need the above (leave the forwarding wan > lan).
Check the local firewalls on your computers - windows in particular will not accept connections from other networks - only the local subnet is allowed by default.
I have an unraid server as one of the servers and had been using that to determine if it all was working or not, clearly that was the mistake, I couldn't use tcpdump to determine if I was actually hitting it. I plugged in a linux laptop and hosted a python webserver and can hit that, so this just seems to be an unraid server issue now.
Thanks heaps for the help! Once I work out the unraid issue Ill add it here as well for completeness.
Glad the routing is working. As I said above, the local firewall rules on the various hosts can make it appear that the routing is not working... but the good news is now you know that's what you need to resolve.
Yeah you saying that, prompted me to try the laptop because I can at least dump the traffic on that, but I didn't even need to get that far once I plugged it in and set up a test server.