I was wondering if activation was some way causing an issue. I did not really want to activate until I had an install I was happy with. But I did try it and I am getting a different message now.
"Windows Media Player encountered a problem while playing the file. For additional assistance, click Web Help."
Again, all the videos, pictures and broadcast work fine on the local LAN from the windows 2008 server. Both LAN and WAN work fine when using 2003.
* As far as the video card I am running this in a virtual machine under VMware VI3. So no real video card. The server is a Dell 2900.
I greatly appreciate the feedback and suggestion. It really seems like some sort of networking issue. Perhaps caused by the way the 2008 version also loads IIS causing a conflict on port 80. I have setup 2 IPs on one NIC to sort out the ports. I think I will get rid of the second IP and just try to manage the ports on one IP. The other thought I am having is that 2008 just does not like NAT on my router.