In light of recent revelations that the government specifically targets for surveillance people who do searches for Tor, here is how I suggest you use Tor:
1) Get one of the VPN services, install it and verify that traffic is sent out by default over the tunnel.
2) Use this link to obtain Tor. Set it up so that it runs as a SOCKS proxy locally (the default way, but you can also install it without a browser as just a proxy
3) Keep the VPN and Tor services running all the time, with the kill switch feature such that if the VPN link goes down, the Internet shuts down.
4) Configure Firefox in private mode (about:config) permanently. Configure it to use the Tor proxy
5) Disable geolocation in all browsers
6) Leave everything else default.
What this means is that all your traffic goes onto the Internet at the remote proxy location. If you don’t torrent, you can even make that exit point in the USA, which may help you do stuff like banking or services which require that you access them from the USA. Or you can just switch VPN endpoints when you need to. Whenever you want to do something with stronger anonymity, run Firefox or the Tor browser. This will put you on the Tor network. By disabling geolocation, you gain some additional protection against Javascript, which is still on in Firefox (turn that off if you don’t need it, but I use Firefox in this was specifically in cases where I need a full-featured browser, but still run it through Tor. Note that Flash will actually bypass proxies, so it will go out through the VPN connection. As as additional safeguard to your anonymity, pay for the VPN service using bitcoin, and use an email anonymizing service such as Guerrilla Mail.
Slightly less Random Ramblings 