On July 15, we owe estimated tax payments for 1Q and 2Q. We have no withholding of any kind. It will be a complicated tax year due to selling a rental in 3Q. Depending on that impact, we may or may not make our usual Roth conversion in 4Q. So, plenty of unknowns as I contemplate how much money to send the IRS in a few days.
In similar situations in the past, I've used the annualized income method to avoid penalties for underwithholding. It's a bit of work, but not too bad. So my first instinct was to send minimal payments for 1Q and 2Q. Then larger payments, as required, in 3Q and 4Q. And clean up the mess with Form 2210 when I file.
But then I remembered that some members here pay tax in December by making an IRA withdrawal with 100% withholding. The IRS considers such withholding to have been made equally throughout the year. DW and I both turn 59.5 this year. So this is the first year we could use this method, which seems very straightforward by comparison. But...
I would have to reduce our Roth conversion by the amount of the IRA withdrawal. Although I suppose that has the same effect in terms of reducing future RMDs. I just don't want to commit to any additional taxable income until I see the impact from the rental sale.
Also, we'd be using the IRA instead of taxable funds to pay conversion tax, which drives 80% of our tax liability. This would negate one of the benefits of Roth conversions. OTOH, it would preserve the taxable account for step-up in basis when one of us goes. That may be a larger benefit, though not much fun to think about.
Just curious, for those who do this, are there other pros and cons that I'm not thinking about?
In similar situations in the past, I've used the annualized income method to avoid penalties for underwithholding. It's a bit of work, but not too bad. So my first instinct was to send minimal payments for 1Q and 2Q. Then larger payments, as required, in 3Q and 4Q. And clean up the mess with Form 2210 when I file.
But then I remembered that some members here pay tax in December by making an IRA withdrawal with 100% withholding. The IRS considers such withholding to have been made equally throughout the year. DW and I both turn 59.5 this year. So this is the first year we could use this method, which seems very straightforward by comparison. But...
I would have to reduce our Roth conversion by the amount of the IRA withdrawal. Although I suppose that has the same effect in terms of reducing future RMDs. I just don't want to commit to any additional taxable income until I see the impact from the rental sale.
Also, we'd be using the IRA instead of taxable funds to pay conversion tax, which drives 80% of our tax liability. This would negate one of the benefits of Roth conversions. OTOH, it would preserve the taxable account for step-up in basis when one of us goes. That may be a larger benefit, though not much fun to think about.
Just curious, for those who do this, are there other pros and cons that I'm not thinking about?