1. For 2019, technically speaking, you are considered as a nonresident as you did not meet the Substantial Presence Test SPT. As TurboTax does not cover nonresident filing, you are advised to contact Sprintax. This is probably the simplest way to go. However, you could file as dual status if you meet the First Year Choice. This way, you would file as a nonresident for the period before you entered the US and a resident from August till December.
To read more about the pros and cons on dual status, click here: Dual status
For instructions how to file Dual status, see DualStatus under "What and Where To File for a Dual-Status Year" and 1040NR.
You can use TurboTax to file your residency portion. If you did not have any stock sales, rental or self employment income, you can simply use theTurboTax Deluxe version. You cannot use any online products for your 2019 taxes as they are designed for 2020 taxes. You have to purchase the download version, click here: 2019 taxes
2. No, you cannot. You have to re-purchase TurboTax program for your 2020 taxes. See explanations here: re-purchase TurboTax program You can purchase either online or desktop. Click here: https://turbotax.intuit.com/
3. TurboTax would not apply for ITIN for your son, unfortunately. Please continue to read:
Without your son's SSN or ITIN, you won't be able to either e-file or paper-file. You need to apply one for him. When you are applying for the ITIN, you can use the TurboTax program to prepare your tax forms and then paper-file them. But you cannot e-file. You will need to submit all your 2019 and 2020 tax forms along with the Form W-7, ITIN application and required documents by mail at the same time.
See here for the instructions how to do so in the TurboTax program:
-In the program, as you enter the information, leave the SSN space blank
-After entering all your information, print out returns and required forms ( write APPLIED in the SSN space)
-As TurboTax does not support the Form W-7, fill out the forms by clicking this link
https://www.irs.gov/Individuals/General-ITIN-Information and attach to other required documents
-Submit all paperwork including your 2019 and 2020 tax forms to IRS Austin location in Texas. ( please see Form W-7 instructions)
For more information about ITIIN, click here: ITIN
@ divcesar
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