road to incarceration is breaking the law. (or I guess being labeled a terrorist)
It's possible to go to jail for the way you use dollars. It's possible to go to jail for the way you use gold/silver. It's possible to go to jail for the way you use bitcoins too I imagine.
In other words, it's your actions/activity that gets you in trouble.
There is a legal section at the forum at bitcointalk.org, as well as lawyers that actively support Bitcoin if you're interested.
Bitcoin is simply a commodity, like Facebook credits. It's true it's now in a sort of legal gray area, undefined. However, it is not illegal to own and use bitcoins (currently).
Also, Bitcoin is global, so it's not completely under the jurisdiction of the U.S.
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