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Peter -- Quick question about the second to last word in your Item #3 -- "tax" years.
I opened up my first/only Roth IRA in December 2017.
Counting "tax years", five of them would be 2017, 2018, 2019, 2020, and 2021.


Thus, if I withdraw earnings on January 1, 2022, have I met the five year test, and the withdrawal is tax free?

Not enough information. Yes, you would meet the appropriate 5 year test. But you also have to be over 59.5 years of age to have a tax and penalty free withdrawal of earnings. For earnings, the test is 5 years AND old enough.

Even though, technically, it's only been four years and a month or so since I made the contribution?

Yep. You can actually get down to 3 years and 8 1/2 months if you make a contribution on April 15 for the prior year. That's why I mention "tax years".

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