Tax Deadline Today: Outrageous Loopholes, Tax Tips for You

April 15, 2009— -- For millions of U.S. taxpayers, perhaps the most dreaded countdown of the year is drawing to a close: Today is the deadline for filing your taxes with the IRS.

While the majority of Americans have already submitted their tax returns, the IRS estimates that at least 20 million -- one in seven tax filers -- are waiting until this week to send in their returns, whether it be by lining up at the local post office or clicking their mouse buttons through tax software or the IRS' own electronic tax forms.

If you're one of them and you have yet to tackle your 1040 form and other paperwork, take heart: ABCNews.com has compiled a list of tips on deductions and time-saving tax tricks.

If you're feeling more adventurous, you can also check out some tax loopholes that saved money for American taxpayers in the past, as well as some that backfired.

But first, what you should know if you're preparing your return now.

File online for free. For the first time, no matter what your income, you can file your tax returns online for free through the IRS Web site at www.irs.gov.

Those who earned less than $56,000 in adjusted gross income in 2008 can also qualify for free software for step-by-step help.

If you're eligible for a tax refund, filing electronically will help you get that cash much more quickly than mailing in your returns.

File for a tax extension but get ready to pay. If you just can't get your returns finished in time, file an extension. Everyone is eligible for an extension, which allows taxpayers six more months -- until Oct. 15 -- to file returns and millions of Americans take advantage of extensions every year.

The bad news is that, like tax returns, extension requests are also due April 15, and filing one doesn't mean you get more time to pay your taxes. It just means you get more time to finish your paperwork. Taxpayers filing extension requests must still estimate roughly how much they owe the IRS (if anything) and send a check for that amount by April 15.

Don't pay too little. If you're in a hurry and filing an extension, a good way to determine how much you owe is to use last year's tax filings as your guide. Given the beating that the recession has given to many people's income and investments, if you owe money at all, chances are you owe less than last year.

But don't drop your estimate too much: If the IRS finds you haven't paid enough, you'll face fees and penalties.

Last year's tax returns will be less helpful if you've had a major life change, like purchasing a house or switching jobs. In that situation, it might be best to consult a tax professional.

Standard deductions make for quick filings. If your financial life isn't a complicated one -- you don't pay interest on a home mortgage, you don't make large charitable contributions, etc. -- you can get your taxes done quickly by filing for a standard deduction instead of itemizing deductions.

For 2008 tax returns, the standard deduction for single individuals is $5,450; for married couples, it's $10,900. Additional standard deductions apply for those over age 65 and with disabilities.

Tax Payment Options and More Can't-Miss Deductions

Don't forget the new real estate tax deduction. There's a new standard tax deduction for homeowners. They can add a standard deduction of up to $1,000 if they pay real estate taxes. This will prove especially beneficial to homeowners who have paid off their mortgages and don't deduct mortgage interest payments from their taxes.

And, if you were a first-time home buyer in 2008, you may be eligible for a tax credit of up to $7,500 or 10 percent of the purchase price, whichever is less.

There is an important catch to this credit, though. You have to pay it back in the next 15 years, in equal amounts each year, which makes it a bit more like a loan than a credit. So if you take the maximum credit of $7,500, you will have to pay back $500 per year for the next 15 years.

But it still helps you get some much needed cash now when the economy is so bad, and you can pay it back a little at a time as things get better.

Deduct job-hunting expenses. If you were laid off in the past year, most of the expenses incurred while looking for a job can be deducted from your taxes, so carefully track these expenses. For example, any money you spent on creating and mailing your resume is deductible.

You can also deduct expenditures for career coaches and headhunters. You can even deduct long distance or cell phone charges related to the job search, as well as travel expenses incurred for interviews, including mileage.

More easy-to-miss deductions and credits. Parents who paid their children's college tuition in 2008 can deduct up to $4,000; teachers who paid for books or other classroom supplies can deduct up to $250; and if you bought a hybrid car or truck, you're eligible for a conservation tax credit of between $250 and $1,000. Depending on the make of your new car, you could also get a fuel economy credit of between $400 and $2,400.

Add to your retirement savings quickly and easily. When filing your tax returns electronically, the IRS allows you to designate which accounts it should transfer your refund to. You can opt to have part or all of your refund transferred to your Individual Retirement Account (IRA) and, if you think the stock market is near its lows, use the money to quickly buy up some low-priced shares.

Don't forget random sources of income. Did you get paid for jury duty? That must be reported in your taxes. Did you have an interest-bearing bank account that you closed sometime in 2008? That interest income should be reported too.

Take advantage of a tax payment plan. In this recession, unfortunately, many Americas don't have enough money to put food on their tables, let alone pay the IRS. Luckily, there is a payment plan option, but it comes with several strings: You may qualify if your tax bill is less than $25,000 and can be paid off within five years.

You will also have to pay interest on your payments, but the rates are typically much more favorable than taking out a loan. The IRS' interest rate is 5 percent. Additionally, if you are approved for a payment plan, you will also be charged a one-time fee of $105.

Paying with plastic? Think twice. More and more people are paying their taxes by credit card this year.

This may seem like a good idea, but you will likely be charged a convenience fee of 2.49 percent on your entire tax bill by one of the approved service providers handling your payment.

On average, Americans owe about $2,200 to the IRS; on this amount, the average convenience surcharge totals nearly $55.

'Creative' Deductions

Now, on to some of the more, let's just say, creative, deductions. Over the years, American taxpayers have tried just about everything and anything to avoid paying the government more money.

Super Bowl Sales Seminar

You can't blame a guy for trying? Well, if you are the IRS, you can.

Back in 1981, Danville Plywood, a Virginia company, sponsored a "Super Bowl Sales Seminar" where it flew 120 people, including customers and some employees along with their spouses and children, to New Orleans.

They paid for airfare, hotel rooms, game tickets and even threw in an outing to the French Quarter.

The company claimed a $103,000 deduction, saying it was an advertising cost. The tax savings: $45,000. The courts ultimately found the expenses had nothing to do with Danville's business and rejected the deduction.

Tax-Free Safari?

O. Carlyle Brock, president of the Sanitary Farms Dairy in Erie, Pa., tried to write off the cost of a six-month hunting trip in Africa with his wife.

Before you call this a scam, consider this: Brock said there was a legitimate business expense.

You see, the dairy -- which bought, processed and sold milk -- ran advertising around the theme of wild animals. Customers were served game dinners at the plant, they shared films of the hunt and displayed heads and skins from hunts in their own museum for the public. They donated a tiger from the Africa trip to the Erie zoo and held a "name-the-tiger" contest. The IRS ruled the trip was a legitimate expense.

Is Laundry Deductible?

Ever think about trying to write off the cost of doing laundry, buying various bath and skin oils or even your daily shampoo? How about your gas and electric bill?

How, you ask? As medical expenses.

In 1968, Earl T. Jefferson tried to deduct all those items after his doctor suggested he sit in tubs of hot water to treat his prostatitis and that he wash his hair and scalp three times a day.

So, he said that buying all those products and heating his shower water were actually medical expenses. The IRS and, subsequently, the courts didn't agree, declaring the expenses to be personal, living and family expenses and, therefore, nondeductible.

Nice try.

Tax Deductions: Special Dentures

Then there is the case of the $3,500 dentures.

In 1935, Edward A. Sparkman purchased two sets of dentures to stop a slight hiss that could have prevented him from receiving future work as an actor. (The second set was a backup so if one broke, he could still act.)

The courts ultimately said the expenditure was "nevertheless, so purely personal in character" that it cannot be considered a legitimate business expense.

The Cat Food Deduction

This is probably one of the most creative -- and shocking -- tax deductions out there.

Samuel T. and Carol A. Seawright had a little problem at their Columbia, S.C., junkyard: snakes and rats.

So, the couple came up with a creative solution. They left out cat food to attract wild cats to the junk yard. Those cats would run off the snakes and rats.

So, was the $300 they spent on cat food a legitimate tax deductions? Turns out it was.

Buffalo Meat and Body Oils

Finally, we bring you one of the most obscure tax cases, which comes from Corey L. Wheir, a professional bodybuilder who tried to deduct high-protein buffalo meat, protein shakes and various kinds of body oils in 1999, 2000 and 2001.

Wheir ate three pounds of buffalo meat a day for muscle development. (If he had stuck to lower-protein beef, he apparently would have needed to consume six pounds a day.) He also consumed protein shakes.

He wrote off all that on his taxes as business expenses.

The court said "there is no doubt that buffalo meat is also consumed as food by nonbodybuilders, albeit not with the regularity and in the quantities consumed by petitioner." It ruled that his consumption was "inherently personal" and therefore not a legitimate deduction.

Additionally, Wheir used a number of oils to help him look better during competitions. The court found that the oils were a legitimate use for his business and, therefore, deductible.

So, as you go through your taxes, consider some of these more unusual loopholes. As always, remember to consult a professional tax advisor. And the only reason we know about these deductions is because they all ended up in court.