This year has warped my conversion schedule. I went flat in March before the big drop and generated a bunch of cap gains taxes. It’s worked out OK. I have a couple hundred K of short term and long term tax loss harvested which I can apply to the gains reducing my tax bill dramatically. In addition I only Roth converted up to the top of the 12% bracket (a little over 100K) to keep my ordinary income tax bill low. Cap gains raises ordinary income taxes beside the capital gains themselves.
There are several calculators I use to estimate taxes.
Tax Plan Calculator is a quick ordinary income tax calculator
Smartasset is a quick cap gains tax estimator
1040 Calculator is a more comprehensive tax estimator.
If you have LTCL (long term cap loss) and STCL short term cap loss, these can be applied to cap gains. STCL can be applied against STCG on a dollar for dollar basis. Accrued STCL can also be applied against LTCG. To do so is an inefficient use of STCG if you incur much STCG in a year. If you hardly ever accrue STCG the using STCL against LTCG may be an option. If you have both STCL and LTCL these can be added together and used against LTCG to reduce your tax bill. Since the CG taxes are likely the lowest I’ll ever see in my life time, I decided to reset my tax basis as well as protect my money during this time of high volatility. Using the capital loss in a low tax environment makes the write off more robust. If you have a 15% cap gain rate and a $1000 cap gain and a $500 cap loss to apply against the gain you wind up paying 15% on $500 of $75. If cap gains were 20% the tax would be $100, so paying in the lower tax environment in this case saves 25% on taxes.
As of tonight a Biden win is likely. Depending on the Senate outcome there could be change in tax policy coming. The most draconian would be a retroactive tax revision in 2021 if House, Senate and Pres all go blue. If Senate stays red, tax law will likely be static through 2022 and may become in play in 2023 but likely won’t take effect till 2024. If Trump wins tax law won’t change till 2025. AS of 2020 I have 67% of my Roth completed, this year in the 12% bracket. Next year in Jan 2021 I can convert up to the top of the 22% bracket and likely be immune from any tax changes. This would take me up to about 82% of my Roth conversion by Jan 2021. The next year 2022 would also be a 22% bracket conversion, taking my conversion to 92% of completion and would likely be still under the trump tax regimen. 2022 is a mid term year and the Senate would be liable to change from red to blue so 2023 may be the year they decided to raise cap gains, but by then I’m in my final year of conversion with only a small amount to convert and a concominent small tax liability.
In 2021 we start SS and so that adds to the conversion ceiling. 2021 will be a small SS check because my wife will retire at 62 taking her age 62 discount and I will take her spousal benefits which is 50% of her take. In 2022 I will turn 70 take my full SS and she will continue with her age 62 payout and we will continue like that until she reaches FRA when she will switch from her benefit to my spousal benefit 50% of my SS, or 150% of my SS. This maximizes our SS over a lifetime and when I die she gets a bigger survival benefit. Therefore 185K (using standard deduction) is about the top of the 22% and (185K – 0.85 * SS) is the Roth conversion ceiling if I want to stay in the 22% bracket.
I’m definitely be ready for this Roth stuff to be over and I’m definitely ready to start SS. My goal is 1.5M in the Roth for self insurance, 400K in a TIRA to RMD as an annuity, Social Security, and then use he brokerage as a piggy bank to pay the difference between SS + RMD and my monthly expense.