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When Should You File Your Taxes With a Tax Professional?

The choice every taxpayer faces this time each year: File your taxes with low-cost software or with a pro?

Low-cost software can likely get you a compliant return if you just have one W-2 and you’re taking the standard deduction.

But compliant does not mean optimized.

Software won’t flag long-term tax planning opportunities or find credits to claim that you weren’t aware of. It also won’t catch your data input errors if you make a typo or misunderstand a tax form. 

And if you receive an IRS notice, most software provides a phone agent who tells you how to handle it. But they won’t talk to the IRS for you (unless you pay extra upfront).  

So, when should you hire a tax pro’s help? I recommend you do so if…

  • You started a side hustle or became self-employed
  • You bought or sold a home
  • You have rental property
  • You received stock options or RSUs
  • You traded crypto
  • You lived or worked in more than one state
  • You received trust or estate distributions
  • You have multiple 1099s, K-1s, or investment accounts

Yes, there’s a price jump when you work with a qualified preparer. 

But that’s because what you’re really paying for is the interpretation of changing tax law, strategic planning across multiple years, and identification of credits and deductions you wouldn’t know to look for.

And if you get an IRS notice, a tax professional knows how to resolve issues efficiently and can take on the IRS for you.

I’m not saying everyone needs to hire a tax professional every year.

Just evaluate the true cost in context. 

How confident are you in interpreting tax rules? And how comfortable would you be taking on the IRS if you received a notice?

If, after considering, you decide professional guidance is the right move for you this tax season, let’s talk:

212-247-9090

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