Americans are known to bristle come April 15, but nearly 240 years after the founders threw a Boston Tea Party to protest unfair taxes, we find other less dramatic – but no less creative – ways to challenge the tax code. Modern-day challenges often end in U.S. Tax Court, where citizens can go to take on the Internal Revenue Service.
The basic questions that get brought up in Tax Court seem straightforward enough: What is income and what are its related expenses? The specifics can get, well, flat-out weird.
The IRS code may be full of loopholes and deductions as it is, but the IRS has also approved more than a few imaginative – even wacky – tax breaks.
If you have a huge deduction that you’d like to take but are unsure if it will pass muster with the IRS, talk to your tax preparer to see if a private letter ruling (PLR), which is written guidance from the IRS that provides an advanced decision on how it would treat the case, makes sense, advises Gil Charney, principal tax researcher at the Tax Institute at H&R Block in Kansas City, Missouri. It does cost money, so make sure the deduction is worth it.