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You would have to open the remote desktop port (default: 3389) on the router (which most likely has a firewall) for the windows 7 machine. This will allow Remote desktop connections from outside networks.
So when you connect from the outside of the local network, you will connect to windows 7 machine.
Then to connect to the server, you will do the remote connection from that windows 7 machine to the server.
Simple diagram for what I'm saying:
Win7 --> Firewall (Port 3389 Open & Redirected to Win7) --> Win7 --> WinServer2008
Since you have an actual server you could create a VPN on the server. This would require you have either a 1. Static IP from your ISP or 2. a DDNS name setup for the redirection. Your router should be set to support vpn pass through. Then you can connect via VPN from the remote computer and use RDP to connect to any machine on the network directly.
Get your facts first, then you can distort them as you please. Mark Twain