I've Windows 7 64bit Pro client in a private LAN behind a Netgear wgr614v7 router. I've also a remote Debian server machine outside. I'd like to tunnel all (or specified ports/protocols) over this outside server, so when I'm on the Windows machine and I request serverfault.com it would not appear from the wgr614v7 public IP but from the server.
But it's not only about HTTP traffic, it's basically about everything I'd like to: other TCP ports, even UDP, etc. It must be transparent to the application, e.g. they shouldn't be aware of this. All their requests just appear as being from the server and the tunnel between them takes care about the packets.
I'm aware of e.g. Putty and forwarding individual ports or using it as a socks proxy, however not many applications to support this and the support in windows itself looks non-existent to me.
I might add it should be something "reasonable" easy to set up. I've heard about PPTP but I'm unsure about it's security implications (by design). Should I go for VPN? There seem to be two common solutions for Linux (OpenSwan and StrongSwan), why would I pick the one over the other? I also fear that setting up a VPN might be quite complex, OTOH maybe it's the only sane way to do the things right? Or is OpenVPN sufficient?
I'm seeking for open (source) solutions, what other options to I have or which direction should I head to?
http://openvpn.net/index.php/access-server/download-openvpn-as.html
Easiest option. Full web-GUI and everything for easy set up, client application is one-click login, and it's free for up to two simultaneous clients.
OpenVPN is certainly the easiest, but you're probably best off setting up a full firewall distribution like Endian. It comes with all the necessary software pre-configured.