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Old 11-11-2011, 12:39 PM
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Section 1244

let's say i invest in a corporation and pay $10 for the qualifying stock and give it a loan of $499,990. When the stock goes bad, I clearly have a $10 1244 loss and a $499,990 non-business bad debt. What if i had a smart tax adviser? What would he advise?
Could i buy additional shares of stock (about $99,990 worth or so) and then utilize my $100,000 worthless stock deduction as an ordinary loss?"



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