Wired has a nice story on a crypto party organized by Edward Snowden shortly before he leaked the NSA documents. He used the same e-mail address to organize this crypto party that he used to contact Glenn Greenwald for the first time, which happened to be 11 days prior to the party. He had even been running Tor exit nodes at the time.
A crypto party is an open, free, and public tutorial on the use of cryptographic technologies, such as Tor, GPG, TrueCrypt, Tails, and others. It looks like a brilliant and practical way to overcome the learning curve of good security.
(Score: 5, Informative) by Common Joe on Sunday May 25 2014, @12:58PM
This goes for everything: if they want you, they will get you. Now, let me ask this question: if they really want to get you, do they need to decrypt your stuff? They'll just throw fake charges at you. Doesn't matter whether they are true or not. Simply accusing you of kiddie porn (even if you don't seek out kiddie porn and even if you don't use Tor) and your life is ruined. The only time they'll really want to decrypt your stuff is if you have something that is really important to them. For a commoner like you and me, they already have all the information they need: credit card transactions, money in the bank, etc.
I don't use Tor often, but when I do, it doesn't seem to be too slow. It will be slower than regular surfing because your information is hopping through several nodes, but that is what keeps you anonymous.
It makes you look more suspicious to common law enforcement should you get caught up in something ugly. So does using TrueCrypt or Linux. They will ask you questions and you'll need to have answers.
That is a personal choice that no one here can answer. Only you (or your Dad) can. Who is to say how secure this is? Not even the maintainers can say with certainty. The NSA thought they were secure and then Snowden came along. So far, to my knowledge, no one has been prosecuted only because they were using Tor. (It would be a tough sell in court.) They will use Tor and everything else crypto related to hang you if "they" think you are guilty of something or don't like you. It will be used to turn popular opinion against you. (Popular opinion may mean a jury.)
Also, I wouldn't really say Windows is secure against people like the NSA. They'll be able to crack your computer if they want bypassing Tor and the rest of it. No proof, only my opinion.
There's a reason why most of us laughed when DARPA [soylentnews.org] said they'd come out with a totally secure drone. It can't be done. Very tough to crack? Yes. Totally secure? Not a chance. There are currently rumors that the NSA has a bunch of exit nodes under their control. That is a weakness of Tor. Allow me to elaborate.
Tor cannot make you totally anonymous. If you look at your email via an unencrypted means and you do so using Tor, your email is totally open between your computer and the entrance node plus the exit node and your email provider. Tor only masks part of the transfer between you and your email provider. In other words, it masks your meta data. In this example, because your data is leaking information about you, you are exposed despite using Tor. If you use encrypted means to access your email and do NOT use Tor, then no one can see your email, but people can know when you are accessing your email, (approximately) how much data is transferred, and how often you check it. If you use encrypted email and Tor to access your email, then you (in theory) are totally masked between your computer and your email provider. (If you use Gmail, Tor and encryption doesn't help you a lot against the government and any entities Gmail may decide to sell your information to. If I use an alias like f.the.nsa@gmail.com and keep out all other private information about myself, then Gmail won't really know who I am. Start leaking information about yourself, and they'll figure out who you are.) If you forget to use Tor just one time, then you are exposed because you can be linked to that particular email address.
Now, if the NSA has a lot of Tor exits under control, they can trace you some of the time and that is enough to expose you "greatly". (Some information is given here [wikipedia.org] but Tor says this is a bit exaggerated). As soon as they figure out that f.the.nsa@gmail.com is run by Common Joe, they know that every access is probably made by Common Joe and they can watch you access gmail. (a.k.a, your meta data is exposed and it Tor is useless.)
There is another potential weakness I've read about. If they have both entrance and exit nodes covered, they can see a blip on the entrance correspond to a blip on the exit. (Mathematically, they can figure this out.) That definitively links Common Joe to f.the.nsa@gmail.com for meta data purposes.
Hope this is what you were looking for.
(By the way, f.the.nsa@gmail.com is not my real email address. I have no idea if it is in use or not, but I wanted to use a different example address than the real one I give out here on Soylent News.)