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I think the biggest fear with using Tor, Onion Routing and the Darknet is that it was all sort of developed by the Navy. I think it provides pockets of government pretty easy access to treasure troves of data.

If you are doing everything bootable, javascript turned off, pgp, encrypted hard drive...I would imagine you would be "okay"...I am no expert. However, I have done a significant amount of research on Tor. It seems that as many here mention, the Exit Node can potentially be identified. Also, if someone was determined, had enough resources, they could also "possibly" "sort of" trace the traffic route. But this is very very hard to do (according to what ive read), and would require a vast amount of resources.

SWIM has been on Tor a few times and found it to be a neat, very useful tool, in and of itself. The ability to essentially obscure your traffic on the ClearNet (regular internet) has alot of potential uses, both good and bad. That said, if you access the DarkNet, there is alot of things on there that people should question who is putting it there. Seems like a very easy way to find people who want to access that stuff, especially if you can only access it using something like Tor. Makes it very clear who is seeking that stuff.