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Not sure exactly where your "what if" question is going. Are you trying to ask if you need to file a tax return? Or are you asking what version of the software to use to prepare your return? Sounds like you have a lot going on, including (maybe) some self-employment income and gambling winnings and losses.
Who has to file?
http://www.irs.gov/uac/Do-I-Need-to-File-a-Tax-Return%3F
WHY DO I HAVE TO PAY? I WANT THE FREE EDITION
The information that you can enter in Free Edition is pretty limited now. Thanks to the new tax laws that began for 2018 returns, there are no more simple Form 1040EZ or 1040A's. Everything goes on a Form 1040 that has three extra "schedules" with it, and if you need any of those schedules, you are not able to use the Free Edition. Using the standard deduction instead of itemizing does NOT mean you will not need any of those schedules.https://ttlc.intuit.com/questions/4511011-what-happened-to-the-1040a-and-1040ez
https://www.irs.gov/forms-pubs/about-form-1040
If you qualify to use it, there is another full-featured free version of the software:
Try Free File:
You qualify if your income was $36,000 or less, or $69,000 or less if active duty military, or if you qualify for Earned Income Credit
https://ttlc.intuit.com/questions/1900583-what-is-turbotax-free-file-program
Note: If you do not qualify to use Free File then you will have to upgrade to Deluxe or higher in the paid versions of the software.
Online Deluxe $60 State software $50
Or—-Use this IRS site for other ways to file for free
https://apps.irs.gov/app/freeFile/
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1siciliano
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usersk166
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