[Kurn, son of Mogh]

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So the question becomes when do you start getting a W2G or a 1099G... and how do you factor this in when determining things such as rake and ultimately expected value

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You don't get a tax form for cash games, only for tournament wins. It is your responsibility to record and report all your income whether or not someone else provides you with a form.

As for rake and expected vale, those are only relevant to your pre-tax profit.