10 Craziest Tax Deductions for 2011

Dallas CPA Ken Sibley has represented his fair share of country preachers over the years, pious seekers who, for the most part, hewed closely to the path of righteousness. Then came one holy man whose travel and entertainment expenses sought the off-road shortcut to tax savings.

"The minister, new to us, wanted to take travel and related costs incurred when the full family traveled the country looking for real estate investment property," Sibley says. "But none was ever found, and none had been purchased for the past several years."

Maybe he was searching for the promised land.

Ah, the wedding tale! This nondeductible expense ploy pops up every year in different guises, sort of like those bridesmaid gowns that come in colors not found in nature that you'll never wear again. Most try to squeeze that $50,000 whopper into business travel and entertainment, or T&E, expenses ("Hey, I invited my clients!"), but some just want it any way they can get it.

"I had a client who insisted on deducting the cost of his wedding," says a Massachusetts CPA. "He could not understand why this was not deductible, and I could not understand where he expected to record it. As a charitable donation? Like he was nice enough to marry her?"

I guess as long as it's not bigamy, it's big of him.

Sometimes tax preparation can involve some off-the-books negotiation, as Don Meyer of the New Jersey Society of CPAs relates.

"The manager and family member of a famous entertainer recommended the purchase of a $2 million building for office and production space, confident that it would be a $2 million write-off for tax purposes that same year," Meyer says. "When the manager found out the truth -- that it would take over 30 years to recover the expense -- the manager was upset, embarrassed and agitated.

"At one point in the drama, a suitcase with a very significant amount of cash appeared as incentive for the accountants to somehow 'make it work.' The suitcase full of money was refused and the extravagant claim never made it onto the tax return -- at least not the one the accountants prepared before they resigned the account!"

Some taxpayers just get a wild hair when it comes to shaving their tax burdens.

"I was preparing a tax return for a state trooper who was trying to deduct everything under the sun," says another Massachusetts CPA. "He had listed haircuts as a deduction. I asked him why he thought haircuts were deductible. He replied that his hair had to be cut short as a requirement of his job."

Did he provide the trooper his tax trim? Naw.

"I responded that your employer probably requires daily bathing, too, but you can't deduct the soap."

Ah, the evergreen home security system ploy. We've seen legitimate home businesses try to claim their dogs and even cats as a security expense. Me-ow! But the Hunter Group in Fair Lawn, N.J., reports that one client had a personal stake in her home security system.

"One client tried to write off the cost of her home security system. Rationale? If the client's home was burglarized and she was killed, she could no longer pay taxes."

Reckon she could write off food and clothing as well.

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