I will preface this by saying that the scenario below is hypothetical as we are still 6-10 years from FIRE. I've recently gotten my SO on board and excited about FIRE so I've been trying to learn as much as possible. I'm at the point where I have our spending needs about as nailed down as I can get them. Our incomes are relatively high and we are just loading up our investments. However, I'm struggling a bit with some of the post-retirement tax concepts being new to them and am hoping you might be able to indulge me in an example to aid in my understanding. My hope is that this will help me determine what breakout at retirement would be best to aim for (401k vs roth vs taxable). The breakout below is about where I hope to be when we retire.
-Age: 40
-800k in taxable investments (>1 year)
-750k in traditional IRA (converted from 401k)
-170k in ROTH IRA
-60k needed for yearly expenses
-Assume 0 wages/other income sources
-80k equity in 300k house, 30 yr fixed mortgage @ 4.5% (I don't think this is relevant?).
-MFJ standard deduction
-No kids
How much can we convert from my tIRA to ROTH IRA each year to avoid all taxes? Is it equal to the amount of the standard deduction + any other tax breaks we can muster up?
Does it make sense to convert more to ROTH than the amount we can move tax-free given future impact of RMDs?
At what point will we owe taxes on the 60k we are taking out of the taxable investments (long terms capital gains)?
Conversions from a tIRA into a Roth IRA are taxed like earned income, while distributions taken from your post-tax investment accounts are subject to the much more favorable capitol gains taxes (typically LTCG if they've been held for a year or more).
Since you asked for a very simplified example...
For couples filing jointly (MFJ) the standard deduction is $24,000. That means you could convert $24,000 from your tIRA into your Roth while paying $0 in taxes, assuming that you also had no earned income during that year. If you wanted to convert a lot more, you'd simply treat it as earned income. For example, if you converted $50,000 in 2019, you'd be taxed on $26k ($50k minus the $24k deduction). A quick-and-dirty tax calculator shows you'd owe $2,739 in taxes on that $50k conversion (again, assuming you had zero other earned income that year). lather, rinse, repeat each year.
As for paying taxes on oyur investments, if you take them out of your Roth IRA 'bucket' you pay $0. If you take them out of your tIRA or taxable investments you would pay whatever the capitol gains rate is. Due to the change with the new tax law, distributions from taxable accounts are no longer tied to your income (which would negligible for this hypothetical retirement scenario), but for MFJ you pay 0% on up to $77,200 of Long-term Capitol Gains (LTCG) each year (through 2025, which is when that provision of the law will (supposedly) expire).
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tl;dr - if you keep your expenses reasonable (and $60k is within that frame), it's very possible to pay almost no federal taxes at all in retirement, provided you don't also have earned income, pensions or SS. Once you have those it changes the calculations considerably. you can use your standard deduction to help "future-proof" your portfolio by converting up to $24k each year into your Roth account from your tIRA. This will allow you to keep paying little/no taxes if they change the tax rates after 2025 (provided they don't also change the Roth distributions, but that would raise holy hell among people who've already paid taxes on that money going in).