1. A trip to Bermuda. Any business convention held in Bermuda can be written off without even showing there was a special reason to hold your business meeting in paradise. And it’s not the only place: Barbados, Costa Rica, Dominica, the Dominican Republic, Grenada, Guyana, Honduras, Jamaica, Saint Lucia, Trinidad and Tobago, Canada, Mexico and all U.S. possessions also fall into this special tax treatment category.
2. Babysitting costs. Believe it or not, you can deduct the cost of a babysitter as a charitable deduction if the mother of the child is leaving the house to do volunteer work for a charity. Which, of course, we all do on a daily basis.
3. A beautiful swimming pool. This one’s a great example of lateral thinking. After being told by his doctor that he needed to exercise (after developing emphysema), one smart fella put in a swimming pool. The deduction was put down as a necessary medical expense and was allowed, along with the various chemicals, heating, cleaning and general upkeep of the pool.
4. Credit card interest payments. Do you work for yourself? Do you own a small company? If you have made interest payments on qualified business purchases made with a credit card, then you might be able to deduct the interest for those. Just remember: don’t co-mingle the business and personal expenses.
5. Fake boobs. This one is infamous. A stripper going by the name of “Chesty Love” used her hard-earned savings to boost the size of her boobs to the eye-popping size of 56-FF (do they even make bras in that size?). She figured it would get her more tips. And the write-off was allowed, being considered a stage prop essential to her act.
6. The costs of moving…the family pet. Whether you’ve got a Great Dane or a Great White Shark, your pet is considered a personal effect. And that’s great news for you: when it comes to expenses relating to any kind of move associated with a job, the tax man says yes. But I suspect hiring a Hummer Limo to move your gerbil across the state may not be looked upon favorably.
7. Mom and Dad’s wallet. Generally, you can only deduct mortgage or student-loan interest if you are legally required to repay the debt. But if parents pay back a child’s student loans, the IRS treats the money as if it was given to the child, who then paid the debt. So, a child who’s not claimed as a dependent can qualify to deduct up to $2,500 of student-loan interest paid by their parents. Remember, mom and dad can’t claim the interest deduction even though they actually foot the bill since they are not liable for the debt.