Crazy Tax Deductions—Part 2 of 2

Here are some more zany tax deductions that didn't work…and some equally zany ones that did. And a few deductions the CPA preparing the taxes offered an opinion on before the taxpayer filed the forms.

Here's some that were rejected by the IRS.

1) Burning Down The Business:
A furniture store owner had unsuccessfully tried for years to sell his business. He finally hired an arsonist and collected $500,000 in insurance money. But things went bad for him when he tried to deduct the $10,000 he paid the arsonist as a "consulting fee." Both men ended up in prison.

2) Did She Tango Her Way Home:
A taxpayer was denied a deduction for dance lessons which she claimed would improve her varicose veins. The reason for the rejection? The IRS claimed the lessons were not medically necessary, the ruling also extending to dance lessons for arthritis and nervous disorders.

3) Fido's Babysitting:
Millions of household dogs in the U.S. are left home alone each day. One taxpayer hired someone to come to his house and watch his dog while he was at work then he tried to deduct the expense using the same rules intended for children and legal dependents. The IRS said 'no way.'

One that got a thumbs up and a thumbs down.

4) Beer vs. Whiskey:
A gas station owner gave his customers free beer and took the cost as a tax deduction. On the other hand, a businessman tried to deduct several cases of whiskey he gave to clients as an entertainment expense. Tax Court ruled that the beer deduction was allowed but the whiskey deduction was denied. [Makes no sense to me, or anyone else for that matter other than the Tax Court judge who made the ruling]

And here are some surprise rulings in favor of the taxpayer.

5) Dairy Cows On Safari:
The owners of a dairy farm tried to write off an African safari as a business expense claiming that some of the dairy's promotional efforts included wild animals. Even though the concept of 'wild dairy cows' is a bit far-fetched, the IRS actually allowed the deduction.

6) Come By For A Swim:
An emphysema patient was told by his doctor that he needed to start exercising. So, the patient installed a swimming pool at his home and deducted it as a 'necessary medical expense.' Even though they turned down the deduction for the tango lessons, the IRS allowed the swimming pool deduction including the cost of various chemicals, cleaning, heating and upkeep.

7) Here, Kitty-Kitty-Kitty:
Junkyard owners had a nasty snake and rat problem. In an attempt to combat it, they set out bowls of pet food each night to attract the feral cats that roamed the area. The cats ate the pet food and also the snakes and rats. Since the cats made the business safer for customers and employees, the IRS allowed the deduction for the pet food.

8) The Bigger…The Better:
An exotic dancer wrote off the cost of breast implants, claiming it was a business expense since bigger breasts equaled bigger tips. The IRS agreed, saying the implants were a stage prop essential to her act.

And finally, some strange deductions the tax preparer ruled on before the taxpayer filed the forms with the IRS.

9) Carrier Pigeons:
A tax payer was so distrustful of technology that he wouldn't use a computer or even a phone. So, he used carrier pigeons to communicate with his business partner across town. He also thought it made sense to deduct all his expenses for the care, feeding, and housing of the carrier pigeons as a business expense. After determining that the businessman had not used technology for communication in the past, the CPA preparing his taxes decided the deduction was fair. No word yet on whether the IRS agreed.

10) A Baby:
A businesswoman tried to deduct the cost of her own baby as a business expense. She used photos of the baby in marketing materials for her business and believed the money she spent on her baby's food, clothing, nanny, diapers and baby powder—a total of about $26,000 for the year—should all count as business expenses. The CPA doing her taxes wrote off the cost of hiring the photographer who took the photos of the baby as well as the baby's stroller and clothing items that carried the company logo which pictured the baby, but she informed her client that the rest of the expenses were not allowed.

11) Hip Replacement For A Dog:
A woman dropped off her tax information to her tax preparer. He noticed an unusually high amount for medical expenses including $8,000 for a 'family dependent' even though she had no spouse or children. The family dependent turned out to be her dog. Because the animal wasn't a medical necessity for the taxpayer, he couldn't let her deduct the cost of the surgery or any of the dog's other expenses.

12) Pole Dancing Lessons:
A man tried to write off the cost of his wife's pole dancing lessons as a business expense under 'meals and entertainment.' The man claimed watching her dance was his after work relaxation and made him better at his job. His tax preparer informed him that the IRS would swiftly deny the $800 deduction.

13) $1,000 Worth Of Evian Water:
A very wealthy woman convinced her doctor to give her a prescription for three bottles of Evian water (specifying the brand) every day and declared $1,095 as a medical deduction on her taxes for the water. Her CPA said that since she still had the prescription note in her files showing it had been prescribed by a doctor it was a permissible expense even though the doctor's note didn't disclose what her medical condition was that required three bottles of Evian water every day.

14) Spanx Shapewear:
A real estate agent who was 'a little bit big on the bottom' (according to her tax preparer) bought several pairs of the Spanx brand slimming underwear because she thought looking smaller would help her sell more houses. Her tax preparer told her there was no proof the Spanx had any impact on her business or income, therefore, it couldn't be considered a legitimate business expense.

15) Recreational Drugs:
One financial planner had a rock band client actually try to deduct an item labeled 'drugs' as a Travel & Entertainment expense. The total cost of the 'drugs' was in the high five-figures. The band's bookkeeper claimed the cost of recreational drugs was necessary and ordinary. Setting aside the fact that possession of the recreational drugs was illegal, the tax preparer advised the band that the IRS would never allow the deduction.

And on that note…Happy Tax Day to everyone!