YES, you can write of a LOT of things, especially in Internet Marketing, and as a self employment.
Furthermore, if you already started working on your own, but not making that much money, you can go for a "from time to time" job, just for insurance, and stuff. At least, this is how you can do it in Germany, not sure about the US, as I think you have problems with proper health insurance
Anyway, if you really want to go Blackhat, and make enough money, go to a second or third country! There you won't have to pay taxes like you have to pay in Germany. You could even skip all the taxes with right connection.
I for myself pay taxes atm, as I'm working with German businesses a lot.