Mmost Americans are always trying to weasel out of paying more than we absolutely have to. The rest are paying lawyers and accountants to do the weaseling for them. There is nothing more American than trying to avoid paying taxes — the American Revolution was based on the question of taxation. There’s a difference between avoiding taxes (which is what we’re doing here) and evading taxes (which is a felony). Here are some useful deductions that few know about.Your fake boobs are tax deductible. Going from a B cup to a D cup may, under the right circumstances, entitle you to a deduction. Exotic dancer Chesty Love (call me a cynic, but I suspect that’s a made-up name) increased the size of her breasts to 56 FF to increase her tips and claimed the cost of the enlargement as a stage prop essential to her act. The IRS allowed it as a legitimate expense. I have been unable to find out if the pain medications from the sore back that resulted were also deductible.
Related to this is the Playmate Party deduction. The owner of a nightclub promotions firm threw a party for his clients complete with underdressed “bunnies” as part of the décor. The IRS accepted this as a legitimate business-related expense.
I imagine that you could use the Playmate Party deduction at a pool party, but if you’re going to deduct your pool, put it down as a medical expense. After his doctor told an emphysema sufferer to exercise, the patient put in a pool and swam in it twice a day. He got to deduct not only the price of the pool but also the chemicals and cleaning of the pool, as well as heating it and general maintenance.
While hanging out at the pool, some people like to oil up, but usually, they can’t deduct the oil as a business expense. Professional bodybuilders can because they use oil to help show off their muscles. I guess if you buy it by the gallon and use it only on yourself, then it’s OK to deduct the cost.
A less obvious business expense is giving away free beer. One IRS case involved a gas station owner who gave away free beer (somehow, I don’t think it was Chimay Rouge, Sierra Nevada Pale Ale or Newcastle Brown) to his customers. The tax people held the giveaway to be a legitimate promotional expense. Tangentially, I’m not sure giving beer to people who are filling up their cars and driving away is a good idea.
However, you need to be careful with alcohol giveaways. One guy gave a couple of cases of whiskey to clients and claimed it as an entertainment expense. This violated state gift-tax laws and was disallowed.
If booze isn’t your thing, say because you deal in illegal drugs, you can still catch a tax break. If you are involved in the importation and distribution of Bolivian Happy Dust, you can’t deduct the cost of security, nor the vials you package the stuff in, nor any rat poison used to cut it. The IRS, however, will allow you to deduct the cost of the actual drugs. I suspect the hard part here is getting a receipt from the cartel.
In the event you need to go to Bolivia or anywhere else in the “ordinary and necessary” course of business, it’s deductible. A dairy farmer wrote off an entire African safari because of the wild animals involved — why do I have the image of a Wisconsin farmer milking a rhino stuck in my head?
Care to travel to Bermuda, but can’t think of a business reason that is Bermuda specific? Don’t worry about it — go. The IRS will allow you to deduct expenses for any convention or business meeting held there. No questions asked. And if Bermuda doesn’t appeal, you can go to Barbados, Costa Rica, Dominica, the Dominican Republic, Grenada, Guyana, Honduras, Jamaica, Saint Lucia, Trinidad and Tobago, Canada, Mexico and all U.S. possessions (e.g., Puerto Rico, American Samoa, Guam) with the same tax treatment. Just our little way of helping out the tourism industries of our neighbors.
Hate flying commercial? Well, do it right, and the IRS will let you deduct a private plane and all related costs. A couple had a rental condo that was seven hours from their house by car. The condo was remotely located, with only one daily flight to and from the nearest airport. So, they bought their own jet. Any trip taken to deal with the condo is deductible.
If they ever get sick of the condo, they can burn it down. This is not only legal, but it is also deductible if you donate it to the local fire department for practice. The drawback is you have to give them the land, too. It’s frowned upon to take the deduction and then build a new house on the site.
If burning the house down is a bit too radical, just deduct the cost of your life partner. One taxpayer, who had several rental properties, claimed a $9,000 deduction for the management services of his live-in girlfriend, who managed the rental units. The IRS allowed $2,500. The rest, said the tax man, counted as nondeductible personal services.