If you are like me, you will be working frantically this weekend to get your taxes done…or at least the extension form that gives you another six months to get your taxes done.

In honor of this historically unpleasant day, let’s look at a few of the less obvious tax breaks.

One deduction that you might want to think twice about is hiring an arsonist to burn down your business in order to collect on insurance money.  That’s a no-no for a number of reasons.  Someone tried to take that deduction once – bad idea.  In another odd ball case, a dentist submitted a fraudulent insurance claim.  After spending a bit of time incarcerated, she was allowed to deduct the cost of repaying the insurance company for the money she fraudulently took as a business expense.



Better tax deductions to consider include the cost of moving your residence due to the loss of a job or finding a new job.  If you can afford a private airplane, you can deduct airplane expenses to check on a rental property.  If that type of deduction is beyond your means, you might be able to deduct swimming pool expenses if you have a medical condition like arthritis that is alleviated by exercising in the pool.  If you try and take that deduction, make sure you have a doctor’s note and an accountant that isn’t afraid of an audit.

If you have a gender-identity disorder such as feeling like a woman trapped in a man’s body, surgeries and hormone therapy can be deducted.  You cannot deduct breast augmentation surgery as that is considered cosmetic surgery…unless your name is Chesty Love and those personal floatation devices are needed for work (seriously, she got the tax break).

The cost of quitting smoking, treatment of alcoholism or losing weight can be deductible as a medical expense.  The mileage you drive to go to Alcoholics Anonymous meeting is also deductible although at a lower mileage rate than for business mileage.  You can go to the IRS.gov website to see current mileage rates.

When going to a conference about your medical condition, the cost of getting to the meeting as well as registration costs are deductible while your hotel room and food costs are not.


If you are trying to have a baby and you are a woman, fertility treatments are deductible, including the legal expenses associated with getting an egg donor.  If you are a man and wish to hire a surrogate, sorry but no deduction.  Being male is not considered a medical condition.

With all medical claims, be sure to get a doctor’s note as well as your accountant’s approval.  If you do your own taxes, call the IRS or stop by one of their regional offices for guidance.


As CV Weekly paper has a few medical marijuana patients and advertisers, I’d be remiss if I didn’t mention the drug dealer who was arrested and imprisoned for selling a potpourri of drugs.  The arrest led to a tax audit that showed his failure to pay $17,000 of taxes due on the illegal activity.  On a subsequent tax return, he was able to get a tax deduction for the payment of those taxes.  He still went to jail.  Tennessee and North Carolina help the random drug dealer to avoid the tax if not the jail time.  You see their Departments of Revenue will sell you stamps to affix to your illegal drugs so that when you are busted, you can at least avoid the tax penalties if not the jail time.  Strangely, less than fifty people have ever purchased those stamps.


Talk to an accountant or the IRS before taking any of the deductions mentioned.  In some cases, you might want to line up a good lawyer too.

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