If I'm going to start using a contracted self-employment type gig (i.e., Shipt, Instacart, etc.), and I have a regular waged job where I receive my W2 at the end of January, am I going to be able to file using TurboTax for free? If not, what TurboTax product might I need to use?
No. You will have to upgrade to TurboTax Self Employed.
But, maybe. TurboTax also has another free product called the Free File Edition (not to be confused with the regular Free Edition). It has free Federal preparation and free State preparation. There is no e-filing fee. It is not available after October 15
The Free file Edition can handle a 1099-NEC or 1099-MISC.
The Free file Edition is more fully-featured than the regular Free Edition. The Free File Edition can prepare Schedule A, C, D, E, and F that the Free Edition cannot.
To qualify for free 2020 federal and state tax returns through the IRS Free File Program delivered by TurboTax, you just need to meet one of these requirements:
The FREE FILE Edition is located at:
https://turbotax.intuit.com/taxfreedom
How to switch and start over in Free file Edition
https://ttlc.intuit.com/questions/2026912-how-do-i-switch-to-turbotax-freedom-edition
FYI ... for the 2021 tax year NONE of the TT free options will work for you since they are not going to participate in the IRS FREE FILE program next year. However, if you otherwise qualify, you can use one of the other 8 IRS FREE FILE offerings that open mid to late January and you must link in thru the IRS web site :
https://www.irs.gov/filing/free-file-do-your-federal-taxes-for-free
Another option is the TT Downloaded/CD versions ... you can use ANY of them. If you don't need a state return then the Basic will do otherwise choose Deluxe and upgrade only if you feel you need more assistance.