How diverse is your investment portfolio? How many different stocks and securities have you sold last year? Were these subject to short term or long term capital gains? Did you rebuy any of those, making the security subject to the wash rule?

If you have a family, a house, multiple W-2s, 1099s, a retirement account, and a 529, things are still pretty “simple”. TurboTax does not let you use their free file if you’ve traded stocks, but for most other products, even some low volume trading in a brokerage account is considered fairly standard.

At the end of the day, it comes down to how organized you are, and how much time it will take you to do data entry. Usually, your tax documents have clear headers, and usually, these match up to the fields in the tax application. But not always, and the more documents you have, the more hours it will take, and the more likely you are to run into a speed bump that will cause frustration.

So, how much is your time worth to you? If it’s worth more to you than the cost of a tax professional, it’s an easy decision.