The ides of March might have been rough on Julius Caesar, but for most Americans, it's April 15—tax time—that causes the most pain. Even if you expect a refund, as 75 percent of Americans do, you dread facing that annual ritual: the endless paper-sorting, the trying search for deductions, the horror of the bottom line, and the mad, last-minute dash to the post office.

Here are eight ideas for making tax season more tolerable and potentially more profitable.


1. GO DIGITAL

By automating your tax preparation and filing, you can save hours of toil. The IRS estimates that the average household will devote 14 to 16 hours to preparing Form 1040 and related forms and schedules, not including schedules A or D. That includes filling out worksheets and forms and checking the math. Intuit, the maker of TurboTax, the best-selling tax-preparation software, says its users will be done in about four hours.

Almost 90 million Americans filed their federal returns electronically last year, the IRS reports. There are lots of good reasons for that. For one, the IRS estimates that it processes refunds for e-filed forms in half the time it takes for paper returns. If you also elect to have the government deposit your refund directly into your bank account, you'll save more time. If you owe money, you can avoid writing and sending a check by using electronic-funds withdrawal. Taxpayers in 37 states and the District of Columbia can file their federal and state returns in one transmission to the IRS. For details, go to www.IRS.gov/efile.

There are also new options to prepare and file your federal forms free online. For the first time, the IRS is offering free, "fillable" electronic versions of Forms 1040, 1040A, and 1040EZ to all taxpayers, regardless of income. They are available through the Free File section of the IRS Web site. If you don't need commercial tax-prep software to walk you through the process, this is a worthwhile option. You can prepare your forms and file them directly with the IRS free.

All the major tax software companies are offering free filing this year from their downloads, CDs, and online versions. As in the past, TaxACT offers free preparation as well, regardless of your income. TurboTax also offers free preparation through a more basic edition. Unlike TaxACT, for instance, it doesn't offer Schedule C for self-employed taxpayers. You can still prepare and file free if your adjusted gross income is $56,000 or less. To participate, you must file through a company listed as an "e-file partner" in the Free File section of the IRS Web site. Otherwise, expect to pay $10 to $35 through commercial tax-prep services for the most common federal forms for individuals.


2. FACE UP TO YOUR TAXES EARLY ON

Even if you're organized, chances are one or two pieces of paper—an earnings statement mistaken for junk mail or a misfiled receipt—have gone astray. Or you may have questions for a tax professional or the IRS. Build in at least two weeks to accommodate those possibilities.

February and early March are good times to chase down missing W-2s, 1099s, and other forms. By law, employers, brokerages, and other companies generally must make available all tax information by Jan. 31, though this year brokerages were given another two weeks to distribute some forms. Not sure if you've got everything? Check last year's tax forms.

Use the early weeks to consider other expenditures that might merit deductions or exclusions. Review a 2008 calendar, ideally one on which you recorded appointments and events. Did you take any part-time or freelance jobs? Did you take on a home-equity loan that charges tax-deductible interest? Did you donate a car or boat worth more than $500? (If so, you'll need to get a statement from the charity regarding the sale price; the IRS is no longer accepting your estimate of the vehicle's value.)

Eva Rosenberg, aka "Taxmama" and author of "Small Business Taxes Made Easy" (McGraw-Hill, 2004) has these additional suggestions: If you use child-care providers, get their addresses, phone numbers, and Social Security numbers now. Make sure you have receipts or bank records for all charitable gifts, which the IRS requires starting this year; if not, call the charity.


3. GET YOUR ACT—AND YOUR RECEIPTS—TOGETHER

If your system of organizing tax papers involves a box labeled "Florsheim" or "Nike," it's time for a filing-system makeover. Tax preparers and accountants say that disorganized receipts and tax forms drive them nuts—and cost their clients money.

Organizing doesn't have to be a high-tech, months-long project. Simply buy an accordion folder and use each section to store documents for a different category—charitable contributions (including the costs of any travel you did for charitable work); W-2 forms from jobs, consulting, and freelance work; Form 1099s; income and expenses from rental properties; and business and job expenses. IRS publication 552, "Recordkeeping for Individuals," outlines the documents you should keep, and for how long.

When you're ready to do your tax return, tally up the materials from each folder section and give a copy of the tally to your tax preparer. Leave the accordion folder—and the shoebox—in the closet.


4. CONSIDER YOUR SALES TAXES

This year, once again, you can deduct either state sales tax or income tax on your federal form, whichever is greater. Don't bother adding up those receipts if you live in a high-income-tax state like California, Massachusetts, Minnesota, or New York. Even a major house-remodeling project, four-star vacation, or new car might not produce enough sales tax to exceed your state income-tax bill.

If you live in a no-income-tax state—Alaska, Florida, Nevada, South Dakota, Texas, Washington, or Wyoming—you'll most likely gain with the sales-tax deduction. You'll most likely gain in New Hampshire or Tennessee too, because they tax only interest and dividends. If you haven't kept sales receipts, the Form 1040 instructions provide a default figure that is based on income and the number of exemptions. In fact, the accountants we spoke with said the IRS's default figure is usually higher than the amount that many people actually spend. (You should still save all records from a home renovation. See No. 6.)

Similarly, most people needn't bother tallying unreimbursed medical expenses for income-tax purposes. You are only allowed to deduct the amount of your medical and dental expenses that exceeds 7.5 percent of your adjusted gross income, and if you have health insurance, you're unlikely to reach that threshold.


5. ASSESS ALTERNATIVE MINIMUM TAX LIABILITY

About 4 million taxpayers are expected to be hit in the 2008 tax-filing season with the Alternative Minimum Tax (AMT). The AMT was originally intended to snare the wealthy with inordinately high tax deductions. But now it's snagging middle-income taxpayers with big families, people who pay lots of state and local income tax, and those with high real-estate taxes.

For tax year 2008, the exemption amount for AMT has increased to $46,200 ($69,950 if married filing jointly, $34,975 if married filing separately). The IRS has a 2008 AMT Assistant that will help you figure out your potential tab.


6. MIND THE COST BASIS

CPAs told us that their top migraine moments involve establishing the cost basis of old investments, including stocks and real estate. The cost basis is the purchase price plus costs associated with selling the investment and any capital improvements in the case of real estate. You pay capital gains tax on the difference between that and your selling price, so the higher the cost basis the less tax you'll owe. This filing season, many folks will likely report losses, not gains. The IRS says you can claim up to $3,000 in investment losses in a given year; the balance can be carried forward to future years.

If you have no original receipts, or if you received the investment as a gift, you'll have to find your cost basis. (The cost basis of inherited property is what it was worth on the day of death.) You'll also need to decide which hurts more: Paying a preparer for an hour or more of sleuthing or chasing down the cost basis yourself.

If you're the do-it-yourself kind, check first with your brokerage or fund company. Adam Banker, a spokesman for Fidelity Investments, says representatives often can provide that information over the telephone. But if it's more challenging—say, you sold several investments—it might take a few days. This year, two TurboTax products—Premier, $50 online, and Home & Business, $75 online—include features designed to help people with complicated basis issues.

If the investment was purchased BCE (Before the Computer Era), you'll need an idea of the year—and ideally the month and day—when the investment was made. The firm's shareholder-services department might be able to provide the historical price. But Bill Abrams, a CPA and partner at Abrams Garfinkel Margolis Bergson, a law firm that operates in New York and California, says it's not worth sweating over small investments. "If it's just $1,000, take your best guess" as to its cost basis, he says. (For more on calculating cost basis, get IRS Publication 551.)

It's always worth calculating a home's cost basis if you sell. If you didn't keep good records of your home renovations, take some time to mentally travel from room to room and on the outside to recall capital improvements and estimate their cost at the time. (Assuming you meet certain criteria, you also get a tax exclusion: $250,000 for individuals, $500,000 for couples filing jointly.)


7. GET AN EXTENSION IF YOU NEED IT

There is no shame in requesting an extension to file, and there's no penalty if you pay your estimated taxes by April 15 and that payment is at least 90 percent of what your final return shows. But remember that the IRS eliminated the tax-deadline snooze button. In the past, you could extend it four months, and then another two. Now there's just one extension deadline—albeit a generous one—to Oct. 15.


8. START ORGANIZING FOR NEXT YEAR

While the year is young, invest in another file folder to organize papers for 2009. Or purchase software like Quicken to keep track of your receipts. The earlier you get organized, the less you'll have to beware the ides of April 2010.