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Last year was the first time I really played significant time online and even though my profits were modest, I decided to hire a tax accountant to make sure everything is (a) legitimate and (b) as legal and financially favorable for me as it can be. The tax laws as they relate to gambling can be very confusing and many judgment calls have to be made about whether you are a professional or not, definition of a session, and other laws you might not know about like if the MAXIMUM balance @ any one time in ALL your poker accounts exceed 10k, you are required by law to fill out paperwork declaring so. So, even if your sum never reached 10k @ the same time, if you had 5k on Stars at any point in the year and 5k on Tilt at any time during the year, you have to fill out a couple of forms. The penalty for not filling out these forms can be quite severe in terms of financial loss and possible prison time.
As a start, I'd advise listening to this recent podcast on the subject and make your own judgment. For me, it was important to hire someone who knows the gambling tax law, not just any tax accountant.
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