Ok first of all this is legal and I have it in writing my friend and I are attacking eachother to get better and not break the law.
Setup I have a VMWare image running BT5R3. It uses VMWare's NAT then my network is behind a router using NAT. From there I am VPN tunneled into work which also uses NAT (I believe). I've come to realize that I have only ever run metasploit from the inside or in a lab but never over the internet.
I'm pretty sure with this scenario a reverse payload wouldn't be possible since it requires the machine to connect back to me. Will this work with any payload at all?