Bob wrote: "Requiring a certain number of specific betting opportunities is only an important consideration if it really matters how well this particular gamble turns out. From a real-world standpoint, I don't think this matters at all."
From a tax standpoint it means everything, because you can't carry forward (or back) gambling losses and expect it to hold up in an audit. If you can only do this once per year, if you win you pay taxes on an $1100 gain, which will likely wipe out your average gain of $50/year if you do it again next year and lose.
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