[gwbas1c]

Think about it this way: What if your VPN operates in another country? It becomes an international issue if Bob wants your VPN to tell them who you are.

On the other hand, if your VPN operates in another country, some websites within your country may block you due to content licensing issues.

[mirimir]

My favorite formula, in constructing nested VPN chains:

1) First VPN, that only my ISP and second VPN see: I choose one that's popular where I live, and commonly used for torrenting, and I have a torrent client up 24/7.

2) Second VPN, that only the first and third VPNs know about: I choose one that does business from a jurisdiction that isn't very friendly with my government and its friends.

3) Third VPN ...

4) Final exit VPN, that only the previous VPN and websites see: I choose one that doesn't attract too much attention. For Mirimir, that's IVPN, because I'm already so associated with it.

[icelancer]

What is your favorite way to create VPN chains in Windows/Linux/OSX?

[mirimir]

I mostly use VirtualBox, or VMware in Windows. pfSense VMs make great VPN gateways. VPN and pf setup are pretty easy with their webGUI. Debian VMs also make great VPN gateways, but setup is harder, and their disk footprint is greater.

I've thought about doing it all in one OS, with iptables or pf to control routing. It'd be lots lighter, but more fragile.

[mirimir]

Another option, if you want more security against exploits, is Qubes. But the hardware requirements are far more restrictive, and the learning curve is steeper.