Category Archives: Tax Planning Strategies

Are you an audit target? Here’s the latest scoop from them that (might) know.

Who’s most likely to get audited by the IRS this year? According to Debra Estrem, Managing Director of the scarily-named Tax Controversy Group at Deloitte Tax LLP, the service is going to be focusing more on the wealthiest taxpayers, but is also going to be focusing on people with unusually large deductions and business losses.

As Ben Steverman wrote for Bloomberg, Estrem sees the IRS including in its list of targets taxpayers with:

–large charitable contributions

–large mortgage interest deductions

–large losses from self-employment ventures

–large incomes

Look at this as the IRS trying to focus its limited resources on Going Where The Money Is. None of this means you cannot have significant mortgage interest deductions, or give a lot to charity, or lose money in a venture that you reasonably believe will eventually become profitable.

But as always–document, document, document.

Want to deduct your driving expenses? Tax court says you better keep excellent records.

A Tax Court case this year drives home the point that there are no shortcuts or bypasses for people wanting to take deductions for using a car for business. The taxpayers who went to court reached one dead end after another in their quest for write-offs, but the case provides a roadmap for anyone looking… Continue Reading

“The Situation” is in a not-so-good tax situation

Did you know that “Jersey Shore” reality show personality Michael Sorrentino, aka “The Situation”, and his brother Marc, grossed almost $9 million in a variety of ventures over four years? Me neither, until I read the U.S. District Court indictment, reported inThe New York Times,charging the brothers with conspiracy and filing false tax returns. Michael… Continue Reading

How Oregon is helping a billionaire save some bacon on Bacon

There are two current mysteries about Francis Bacon’s Three Studies of Lucien Freud. First, who paid $142.4 million, the most ever paid for a work of art at auction, in November for the triptych? Second, why is it currently being displayed a mere three miles from my home, in the well-regarded-but-let’s-face-it-not-internationally-renowned Portland Art Museum? Can’t… Continue Reading

Apple avoids billions in taxes, and it all looks legal; those guys really are smart

Lawmakers are using words like “gimmicks” and “schemes” to describe how Apple Corporation has used a web of subsidiaries spanning the globe to avoid taxes. There are hearings this week at which Congressmen are expected to say they are shocked, shocked, to hear of tax loopholes being exploited. As The New York Times reported, Congressional… Continue Reading

Sex and the IRS: making “friends” with your IRS auditor, extreme version

Dear IRS: I’ve Read About This In Your Manuals, But I Never Thought It Would Happen To Me… Sometimes I sort through tedious tax court cases looking for some mildly interesting nugget to share, and sometimes a thing of sheer weirdness lands in my lap. An Oregon man has filed a lawsuit claiming that an… Continue Reading