Tax advice from a computer: Do you need tax software? Five questions to ask.

3. How complicated are your taxes?

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    Prospective buyer Adrian Carter (left) of Chapel Hill, N.C., toured an apartment in the Beacon Hill area of Boston as real estate agent Mike McGrory looked on in this March 2008 photo. Mr. Carter was considering buying a rental property as an investment. Owning rental property can make filing taxes more complicated.
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If you’ve got a long list of stocks, bonds, write-offs, or rental properties, you may decide to pay for a little handholding. Tax professionals know the drill, and most tax software will take you through every possible consideration, step by step.

“If they’ve got anything more complicated than just one income statement then they should seek professional help,” says David Robbins, a partner at Nieminski Robbins & Associates, a certified public accounting firm in Chicago.

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