14 Nice-try Tax Breaks Rejected by Uncle Sam

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A Little Peace and Quiet

You’d think that a tax preparer wouldn’t get in trouble with Uncle Sam… but one of them did, and we can’t help but chuckle at this incident.

She was apparently very busy during tax season, so much so that her clients used to call her constantly, day and night, to ask for advice. Understandably, she wanted some peace and quiet so she occasionally booked a hotel room in order to rest. Not so understandably, she then went on to deduct those costs as business expenses.

She should have seen this coming, as the Tax Court stood firm on their decision that her rest and relaxation were nondeductible personal expenses.

Investigating Daddy’s Mysterious Death

One man had a grueling experience as a child when his father died. Sadly, he did not know whether he’d committed suicide or was murdered, so he paid millions of dollars on a quest to find out by paying experts and private investigators.

Thinking that with enough evidence he could turn this story into a movie or a book, he deducted the payments on Schedule C as a business expense. The Tax Court ultimately ruled that this was actually a hobby and not a business expense.

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