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That said, there's no one like the ultra wealthy to be ultra cheap. I'm also skeptical the issue was over trying to create a tax loss, because, if he's been losing money every year on the horses, the IRS likely doesn't let him claim them as deductions anymore anyway. Hobby loss, or something like that. If anyone's interested, this article explains profit and loss in the horse business pretty well: https://asci.uvm.edu/equine/law/horselaw/hobby.htm The particular one that I think would make it hard for the Mattress King to declare the racing expenses a loss against his other income is: "8. Taxpayer's financial status. The fact that the taxpayer does not have substantial income unrelated to the horse activities may indicate that the activity is engaged in for a profit. The cases in which the IRS challenges deductions under the hobby rule are cases in which the taxpayer has a very substantial income from sources unrelated to the horse activity."
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