We are happy here to give our CPA friends their due. A closely held company recently had a bad surprise when the IRS disallowed the premiums paid for some admittedly exotic business-continuation insurance policies. The off-shore policies had a number of unusual attributes, so that the IRS would not recognize them as “ordinary” and characterized them as more of an estate planning scheme than a legitimate business expense. A federal judge agreed.
Without taking sides in that story, the lesson is that all investments or expenses of any importance should be carefully vetted and characterized by your CPA.
And if the IRS disagrees with the expert accountant, there are always appellate attorneys to appeal that in court.
(PS: Yes, the company in question was in Texas; and yes, it operates in the oil and gas industry. But there does not appear to be anyone named Ewing involved.)