So now that there's another "bubble" at full speed, I'm reaching a point where crossing $100 will mean that me as well as others are making some serious money (I'll leave up to you to define what serious money is)
My concern now is, what if i want to sell and withdraw the money to my US Bank Account.
How do I avoid uncle sam to stick its hand in my cookie jar and takes the tax share?
What if I don't report it?
What if I transfer small amounts ($1000 at a time ever week or so..)
Any accountants in the forum to help me do the laundry?

I don't like taxes either, but as far as I know, most Bitcoin users aren't anarchists, they are Libertarians (I'm a moderate Libertarian), so why not pay the tax? The government may be to large, but you are still getting a service and need to pay what you owe.