Multiple Router Port Forwarding Media Server Questions

[skillz83 0]

Hello,

 

I've looked around, tried many configurations, and haven't been able to solve my problem.  I'm trying to run a Plex Media Server to a Raspberry Pi.  I've got Plex and the Pi running, and I even transferred a setup file from my server machine to the pi prior to running into issues.  I can't get the server and the pi to communicate properly with respect to the media library.  Setup is as follows:

 

ISP Modem ---> Apple Airport Express Router (provides non-vpn wifi) ---> Linksys Router running DD-WRT and AirVPN ----> Both my Plex Media Server Machine (FreeBSD laptop) and Raspberry Pi hardwired in.

 

1.  Do I need to worry about remote port forwarding through the website if the traffic is just going from the laptop to the pi?

2.  Which ports (remote vs. local), if any, should be forwarded within router firmware?

3.  If the above is required, should DD-WRT port forwarding be accomplished using the NAT/QoS tab range port forwarding option or by using iptables in the firewall?  Will using both cause any conflicts?

4.  If I need to use the port listener, please advise if I need to run it from the FreeBSD laptop (which version?) or if I can use an OSX laptop that I use to talk to the Airport Express.

 

Thanks in advance for your time, and sorry if I've missed the answer elsewhere.