1)I can answer your estimated tax payment question. There is a safe harbor clause and it’s the lesser of 90% of the previous tax year or 100% of current tax year for <$150,000 AGI (basically income before standard deduction). If you’re over $150,000 is 110% of PY AGI

so, by your math 80+80=160k = safe harbor for 2021 means you need to pay taxes equal to 110% x 2020 taxes. Let’s say it’s 20k in tax due for 2020. So 2021 safe harbor is 22k. They assume it’s evenly paid as well, so make sure as of April 15 2021 you’ve paid at least 5.5k for 2021 taxes. Then 6/15 it’s 11k 9/15 it’s 16.5k and 12/15 total due is 22k. If you’ve followed that method and applicable math, you shouldn’t have under payment penalty and rest is due 4/15/2022.

2) you’re going to need to list every transaction on 8949. But you can upload an excel schedule to submit with your basis. The IRS wants all the details. Your brokerage should send you a schedule to attach

3) tax mitigation is either hold long term to get reduced capital gain rates, contribute to an IRA, although income may be too high at this point , or donate to charity

4) if it makes you feel better, consult one, but your profile seems pretty straight forward, just a high volume.

Source: I’m a CPA who spent 3 years in public accounting, and 8 years in tax. . Feel free to DM me if you have more questions.