I want to add one more thing: cryptoheaven. It's a nice client-based email in Canada, all of the in-between communication in the middle is encrypted with AES 256. On top of that, you really don't have to register. Fake names, no email verification, and no IP-logging. And to further add icing to the cake: you can literally self-destruct your account on the whim of your finger.
http://cryptoheaven.com/- I often use openVPN but with PhantomPeer - untraceable. And it doesn't reside in the US. Most people will pay via PayPal or CC. But to add anonymity - use bitcoin: US can't do jackshit about it.
- Yes, I often get DNS leak with freeVPN via openVPN. This is why I use PhantomPeer (pay in Bitcoin only).
- Bitmessages - untraceable because it's a decentralized email client. Use Proxies and/or Tor to add anonymity (Bitmessages will work with Tor).
- Mac Changer? Not a big fan of it. Useful, but not really.
- VMware: I put it inside my encrypted system drive (internally or externally, doesn't matter). So if I see something went wrong, just delete the VM files. You're good to go.