@rlwremo wrote:
in #1 above, will I have a penalty because I didn't make any estimated taxes on the untaxed income?
Yes, a penalty and interest.
I guess same applies to #2, if my "estimated" payment is insufficient, would I owe a penalty on top of what I pay when I file my taxes by April 15?
Yes, a penalty and interest, if your estimated tax payment is insufficient.
You will not owe penalties and interest if your total withholding in 2020 is at least 90% of the total tax on your 2020 tax return, or 100% of the total tax on your 2019 tax return (110% if your 2019 AGI was more than $150,000), but it doesn't sound like that will be the case.
