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I switched my yearly conversions from Regular IRA to Roth IRA to the very end of the year, so I can now more accurately calculate the maximum amount I can convert and still stay within my tax bracket and/or MAGI constraints.
Getting into it on a more granular level, I started closely tracking, on a monthly and quarterly basis, each category of taxable investment income (divs, cap gains/losses, short-term, long-term, interest, etc) from my brokerage accounts, so I can see a running total at-a-glance in my spreadsheet.
This is especially helpful as December rolls around and the various divs and cap gains are paid out, some at the very end of the month.
The hardest part for me is being patient and waiting. Conversions are like the gift that keeps on giving.
I did a large one earlier in the year, then two more after seeing the market goes up using TurboTax. At least all the gain on the large conversion is not taxed.
I'm also keeping a running total of each line item of my 1040 up to the AGI and including Schedule D, using the same spreadsheet I track monthly/quarterly divs, interest, cap gains realized. I account for everything, including the yearly long term carryover loss, which goes directly against ordinary income in the current tax year, plus any credits I'm entitled to. I have a field in my spreadsheet that keeps a running total of MAGI, and as that field updates another field calculates the amount that is left over to convert to Roth, in order to hit a specific income target identified at the beginning of the tax year.
I moved quite a bit from my Ira to my roth yesterday. It’s going to take me several years, but I don’t want to go over the 24% tax bracket. I feel (like most others that are converting) that the current tax rates aren’t sustainable and will rise. On top of that my state (il) has no state income tax on retirement accounts (or pensions). I feel that that is going to change too.
I'd like to convert even more, but I'm constraining taxable income for ACA, and that's the higher priority.
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