Wow - thanks for all this depth! Just some follow on questions:
1. How can I be 9 months late on the 15 April 2021 payment, if I made my IRA withdrawal in May 2021?
2. Regarding "My suggestion is to pay as much as you can now and try and get to that 90% figure or the 110% figure from last year". I am not entirely certain which years and which amounts are being referenced here. One estimated quarterly tax payment on the taxes resulting from my May 2021 withdrawal is about $10K = (.90*44K)/4. Only by around October 2022 will I have around $10K in cash.
3. Regarding this "My suggestion is to pay as much as you can now and try and get to that 90% figure or the 110% figure from last year. Then you would only have 1 month of penalties (if the payment is made by February 15)." would you recommend that I withdraw again from my IRA and/or brokerage account to achieve this? Doing so will almost wipe out my assets, and will also have tax implications for 2022 tax year...
4. Regarding "The real question is, are you willing to pay the tax you owe, or do you want to reduce your tax bill.". I want to get out of this debt as soon as possible, but also have to balance realities such as fact that whole reason I moved to Moscow was to try and gain partial custody of biological son, which is legally expensive in unforeseen ways. Also I spent week in COVID treatment center in Moscow and now blood tests are indicating various issues perhaps COVID induced, and so I may have health costs to consider. Plus in general, just seems daunting to nearly wipe out my remaining assets to pay this bill on time. So I am trying to find some compromise, and maybe OIC really makes sense.
Curious: Does the IRS have an online tool that lets you see in real time your debt status (penalties, interest, etc)?
Thanks again - this is really helping me deliberate over options. Lots of nuances.
