I'm not convinced signing up with one of the existing VPN services is any significantly easier than signing up with Digital Ocean or Rackspace, and using the Tinfoil creator service. Have you tried it?
I’m happy to pay somebody 5/mo to handle that + patching etc. etc.
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.