This isn't really a "what's the best program to" question, but more of a "what's the best network design approach" type of question.
Be warned, this will be fairly long.
Problem: In an age where gov't and corporate monitoring of our activities is routine, and where it is increasingly common for lawyers and courts to grab our online data to be used in such mundane/routine things as divorce cases, I shudder when thinking of the future. Mentally fast forwarding 10 years or so paints a scary picture.
Call me a slippery slope nut, but I see our online activities becoming more and more accessible in future years. Though I'm not doing anything illegal, I don't want some future bitter wife or some gov't or private investigator knowing every site I visit while online.
The threat: How easy would it be to gain a complete record of everything I do online?
My first issue is my ISP. My ISP knows everywhere I go. Sorry, I don't trust my ISP. With companies as large as Verizon wholly engaged in literally illegal monitoring of people's phone calls, given our corrupt gov'ts "national security letters", hell, I'd never even know if my ISP was giving up data about me.
Okay, so it's extremely unlikely that the gov't would be serving up nat'l security letters on me. But I think my ISP would give up any information on me at the drop of a hat if threatened with a couple of bills for lawyers' hours. And that more reasonable scenario could happen for any civil lawsuit.
How to obfuscate my online trail: Many people use Tor to hide their online activities. That's nice, and I use Tor too. But for me, Tor has a few drawbacks.
I typically access the Internet with my laptop. At home I route all access out through a GNU/Linux gateway server. My laptop is configured to use that gateway. When I'm not at home it means I have to disable my normal configuration and access the net "exposed".
My idea: Why not configure my laptop to access a remote server that's easily accessible and always available on the Internet? And gee, I have access to such a server. That way, I use the same configuration both at home and away from home.
Okay, great, but what's the best technique? (We're finally coming to the point of this post!) What's the best method to access the remote Internet server?
Here's what I think my choices are:
1) Set up a Squid proxy on the Internet server. Access Squid with a password (to keep twits from using it) and route all traffic out to the Internet server.
Questions/drawbacks. Would I be revealing myself by using my ISP's DNS server? If so, just use the Internet server's DNS server. Would the http traffic be much of an exposure?
2) Set up Tor on the Internet server and use that.
Questions/drawbacks. Would the Tor link to the Internet server be secure/encrypted?
3) Use an ssh tunnel to route all traffic to the Internet server.
Questions/drawbacks. Ease of setup? Some sites/networks I use block ssh traffic.
Clearly no matter what I do nothing will be 100% bulletproof. And of course the Internet server will hold all the data. But that's not terrible, because the main purpose here is just to keep my data from being on an "easily" accessible site like my ISP. I just want to make things difficult for records to be kept and since I'm lazy I want to be easy to setup and maintain.
So here are my questions for you:
• Are there any methods/tools/approaches that I'm overlooking?
• What method would you use and why?