Getting your money out....

[StellarWind]

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Maybe moving 40-50k at one time isn't a good idea. Is a better option to make multiple 4-5k withdrawls and pay taxes quarterly? Or just make small withdrawls and report it for next years taxes?

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The tax you owe, when you owe it, and whether you should make quarterly payments have nothing to do with how or when you withdraw the money. You acquired taxable income the instant you won. Even if you never cash out you owe taxes for the year you won the money.

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Also, I don't have a "real" job, does this change anything? Could I claim to be a professional or claim this as a small bussiness?

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I don't know your situation. But if you don't think of yourself as a pro I doubt the IRS will either. Being unemployed and hitting a jackpot (is that what you did?) is not enough to turn a recreational poker player into a pro.

Besides, I think you should be assembling evidence that you are *not* a pro. Gambling winnings are not subject to social security tax including the employer's share. Pros do have to pay social security tax. What deductions does an online player have that could offset that?