Like an idiot, in 2016, I somehow didn't push the button in TurboTax to claim the $ from investments that I sold. The government hit me with a tax bill and penalties for which I'm on a payment plan on right now. If I went back to amend my 2016 return, would that be advisable? Or do you think the IRS would say, "Oh wait, an amended return! You still owe us taxes on $38K." Am I making sense.
Take a good look at the tax bill for 2016 they sent you.
Also get a transcript from IRS for 2016. https://www.irs.gov/individuals/get-transcript
The reason for this is when IRS sees stock sales NOT reported they many times give you a $0 cost basis and tax it at Short-term gain, when you have a cost basis and it should be long-term.
So YES, if that is the case I would Amend and the tax on the return is actually what is assessed on the tax transcript by IRS.
Take a good look at the tax bill for 2016 they sent you.
Also get a transcript from IRS for 2016. https://www.irs.gov/individuals/get-transcript
The reason for this is when IRS sees stock sales NOT reported they many times give you a $0 cost basis and tax it at Short-term gain, when you have a cost basis and it should be long-term.
So YES, if that is the case I would Amend and the tax on the return is actually what is assessed on the tax transcript by IRS.
Thank you so much for your quick and thorough response!