Softening the Ordeal With Software
If filling out tax forms seems like spending a week in jail, consider using tax software.
It can simplify the process, eliminate math mistakes, and possibly shorten your stay in tax-accounting prison.
Tax software uses a simple approach. First, you fill out basic information found on your W-2 forms, then the program interviews you. As you answer the questions, the software fills out the tax forms automatically.
This doesn't make the process fun, exactly, but it's a little less overwhelming. And if you're superorganized, with all the proper receipts at hand, you can probably finish in half the time.
Two programs lead the pack: TurboTax from Intuit and Kiplinger TaxCut from Block Financial. Both come in basic and deluxe editions for both Windows and Macintosh versions. (The Macintosh version of TurboTax is called MacInTax.)
Your choice depends on what you need.
If your taxes are complicated and you need comprehensive help, consider the deluxe edition of industry-leading TurboTax. Years of refinements make this an elegant yet streamlined program. There are plenty of directions from Internal Revenue Service publications, helpful videos by two tax experts, and the contents of two books: "Money Magazine's Income Tax Handbook" and "How to Pay Zero Taxes." Cost: $50.
Cheaper - especially if you just need the basics - is Kiplinger Tax Cut. The basic version works almost as well as TurboTax for about $10. And it includes free, electronic filing, usually about $10. (Look for special pricing from retailers.)
It's a great deal: tax software plus the benefits of electronic filing for $10. Both Intuit and Block Financial sell state tax programs separately.