[hexeater]

I have gotten IRS penalties/interest due to my incorrectly reporting. I was confused about how to report RSU and Stock Option income, and then I was doubly confused about how to do quarterly filings.

I am REALLY trying to do this on my own without an accountant. I think I got it right with 2019, but I will find in a few week how far off I am when I try to file.

I'd say my interaction feels like the IRS is just painting by numbers - they are just running the numbers and checking if you filed correctly or not. If you did not and the number is significant, they send you a letter.

[iudqnolq]

A trick for when you're trying a strategy you aren't sure of:

you can overpay the IRS by the amount you would pay if the exceptions you are pretty sure apply actually didn't.

They will return the extra to you, and you lose the interest that money could have earned but gain the knowledge for next year of whether you can or can't do what you wanted to try. Depending on your specifics might be cheaper than a tax adviser.

Disclaimer: YMMV, I'm not a tax advisor, I pulled this out of my * * *, etc.