You need to determine who your adversary is (at least the category of adversary they're in).
If your adversary is The NSA, you're probably fucked already - get off the internet.
If your adversary is your local drug or anti-terror law enforcement, they're probably getting "hints" from the NSA and likely parallel reconstructing evidence against you based on that.
If your adversary is closer to local cops, MPAA/RIAA, your boss, your parents, your ex-wife's lawyer, or your ISP - this list provides a great deal of useful information.
Browser/cookie hygiene is orthogonal to VPN/network hygiene.
The steps are: 1) Make a DigitalOcean or Rackspace account. 2) Make an API key by clicking <link> and hitting the button. 3) Insert it in this box. 4) Hit go.
That's it. Then you download/install the client (like you would with any other VPN service) and you're done. You don't need to know anything about the droplet size, or anything else.
Quite literally, my mom has done this, and she sells clothing for a living and is not technically adept.
I’m happy to pay somebody 5/mo to handle that + patching etc. etc.