Thanks for the advice Seleuceia, the evening I posted this we did get the game to work by using Ironclad Online instead of using the multiplayer option and connect by IP address. This was the way my friend always played the game and was surprised it did not work as usual.
I did get to play a game that night and was looking forward to trying again this evening. I checked and while I was able to chat with a couple people on the trinity lobby any games I found were all unavailable.
I decided that since I already had trinity and stardock has a good deal on rebellion for players who own it I said why not... just get rebellion and get involved where all the players must be.
So I buy Rebellion, download it with steam and now I can not even connect through Ironclad Online... It does not even give me the chance to log in it just pops up a "Disconnected From Server" almost instantly.
I will keep digging for solutions but seriously a game that is multiplayer should have a much more intuitive connection.