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Large unplanned LT cap. gain 2022. Should a 1040-ES be filed; to pay taxes now?

Stuff happens, eh? An unanticipated LT capital gains from a real estate transaction (land, not a primary residence) will take place in 2022. We're familiar and comfortable with processing the 2022 taxes at a federal and state level; for cost basis calculations and related. However, the dollar value will be significantly higher than normal and will have an impact upon our "taxes due"for 2022, versus a "normal" tax year. We do understand that line entry items for "traditional" taxable income, versus "LT capital gains" will have different impact(s) on the taxes owed; but will show up in the final math for taxes. A consideration is doing a "test" filing account in our 2021 tax program to obtain an idea of the Fed. tax burden.

We've begun to sniff around the internet for clues of the best path forward to avoid "underpayment/penalties". The IRS site offers information regarding doing calculations (what if scenarios) as to paying taxes before filing time via the 1040-ES. Numerous other online sites offer pieces of information as to a proper plan to avoid underpayment/penalties. A fairly common suggestion is to pay "110%" of ones prior year Fed. taxes now. We read these as a "good faith" gesture towards the IRS, that we know we'll need to pay more in taxes for 2022, but we're not yet sure of how much more. The "gesture" being a way to avoid an underpayment penalty.

Gross taxable income basis for the household arrives "only" from pensions, RMDs and SS. All other investment distributions are in IRAs; therefore, no taxable cap. gains are ever a part of our tax schedules. 2022 will be an non-normal tax filing year.
So, continuing to "sniff" around for a best path forward; which may likely contain paying estimated taxes before year end, for the full 2022 tax year.

Suggestions welcomed as to the best path forward, from your knowledge/experience.

Thank you.

Remain curious,
Catch

Comments

  • Thanks @yogibearbull
    I have read about the payment methods.
    Then you are suggesting that an estimated tax be paid now, eh?
  • I am not a tax professional. What follows is simply my experience: The fourth estimated tax payment for 2022 is due Jan 15th 2023. So you can be quite precise about what you owe by then. But... the IRS says they will not punish a tax payer who pays in estimated taxes 100% of the tax due the previous year. So, whether in quarterly payments as I do, or in a lump sum, as my dad preferred doing, so long as you send the IRS estimated taxes equal to 100% of what your tax bill was in 2021, you are likely to be in accord with the rules of the IRS. You can pay the balance when you file your 2022 return some time before 4/15/ 2022. I hope this is helpful (I also hope it's accurate!)
  • Thanks @Ben
    Your summary is in line with our understanding, too. Although not of consequence; one may pay estimated taxes at any time; not having to follow quarterly ending dates, to the best of our understanding. But, your note about Jan. 15th, 2023 is important, too; as we will fully know the tax impact at that time.
  • edited July 2022
    Only taxes withheld (W-2, 1099, etc) are considered evenly applied and one can do over-withholding from paychecks, IRA or pension withdrawals, etc to avoid penalties related to other income. Otherwise, estimated taxes must be paid quarterly on other income to avoid penalty. IRS would calculate penalty if you don't calculate/include it.
  • I am fairly certain if you pay 100% of your 2021 total on time, there will be no penalty regardless of your 2022 income.

    If you take RMDs, you can pay all of your estimates taxes at the end of the year and have it count for entire year without penalty. Ask your brokerage to send the amount you determine is due to the IRS as a tax payment. Just make sure you file for the withdrawal with enough time for them to process it before 12/31/2022

    This also reduces the value of your IRA, making next years RMD lower.
  • Generally, with lots of exceptions, the IRS expects you to pay your taxes equally in each quarter. That should be pretty obvious, because otherwise everyone would skip their first three estimates and just pay everything on the last estimate.
    For estimated tax purposes, the year is divided into four payment periods. Each period has a specific payment due date. If you don’t pay enough tax by the due date of each of the payment periods, you may be charged a penalty even if you are due a refund when you file your income tax return.
    IRS Pub 505, When to Pay Estimated Taxes

    As Yogi wrote, withholdings are usually considered evenly applied. But if it advantageous to do so (e.g. if your withholdings are front loaded), "you may choose to include your withholding according to the actual dates on which the amounts will be withheld." Pub 505, instructions for Worksheet 2-7, line 31.

    However you choose to allocate withholdings, so long as you've paid in (estimates plus withholdings) of at least 1/4 of the total as of the first estimate deadline, 1/2 as of the 2nd estimate deadline, and 3/4 as of the third, the IRS doesn't care if these payments are even or not. However, if you back load the payments, the IRS does care. Unless your income was correspondingly back loaded.

    If your income was, say $15K in the first quarter, $15K in the second quarter, $15K in the third quarter, and (due to YE divs and cap gains) $45K in the last quarter, the IRS will allow you to pay in roughly half of your taxes in the last quarter.

    See Form 2210 for how the underpayment penalty is calculated, quarter by quarter. It has a Schedule AI (annualized income) where you can document how much income you received in each quarter. Based on those amounts, it adjusts how much you should have paid each quarter.

    This is not the easiest form to fill out and requires fairly detailed bookkeeping (e.g. how much interest did your bank pay you in April and May?). Like Ben, I am not a professional, but I have tried this at home more than a couple of times. I found it something to avoid unless one's income is very uneven.

    Still, it provides an escape in case you wind up with a lot of unexpected income in a quarter.
  • Thanks @sma3
    What we've done over the years is to not withhold much tax from the monthly pension payments, knowing we will underpay for the year; but when pulling the RMD's for the IRA's in December, we withhold extra tax for these distributions. This maintains our tax obligation amount for the year; and we have a bit of extra money monthly from the pensions. Fidelity makes it easy to set how much Fed. and state tax to pull for the RMD distributions.
    Thanks @msf
    I'll look at your links, as I already have a few saved from the IRS site for further study. I'm going to peek inside last years tax program, too; for any guidance there. As this capital gains event will take place during the 3rd quarter, we don't have flex via earlier calendar periods to pay estimated taxes then. As we are retired, we don't have a method to withhold more taxes from employment income, for an offset.
  • About paying equal amounts quarterly vs one lump sum: In retirement my dad paid estimated taxes in a lump sum before the due date of the *first* quarter. The IRS was not made to wait until the end of the year and they never made a fuss.

    Similarly, if one pays unequal amounts during the 4 quarters and the inequality consists of paying *more* than what was expected, I think it likely that the IRS will not complain. That said, their computers may complain. I know a bookkeeper at a law firm who received a notice from the IRS that a heavy fine was about to be imposed because the firm had OVERPAID their taxes. And the amount of discrepancy was less than a dollar. A phone call to a reasonable person at the IRS solved the dilemma in less than a minute.
  • @Ben is correct. So long as one pays more than required each quarter, whether that is everything in the first quarter or just paying a bit of excess in the first three quarters, everything should be fine. It's only when you make more money YTD than your estimates YTD cover that the IRS gets fidgety. Aside from computer glitches.
  • @catch22: one other consequence of a one-time jump in taxable income is your Medicare premium rate, which is income-based. The premium is automatically jacked up, regardless of the reason, and stays there even if that year is an exception. In time, your premium will revert to the appropriate level, but not immediately. Fortunately, there is an IRS form whose purpose is to "appeal" the higher rate. This happened to me and by filing the form I was able to pay just one year of higher premiums. Good luck with your transaction and tax return.
  • Any chance to spread the real estate CG. payment, over two or more years to ease the pain ?
  • Hi @BenWP Thank you. Yes, the Medicare IRMAA factor. Pleased you shared the IRS appeal form, if needed.
    Bonsoir,
    Catch
  • Hi @Derf, No. This is a one time transaction.
    Take care,
    Catch
  • @Derf: it used to be possible to average one’s income over 4-5 years, thereby reducing the pain from a big spike. The IRS did away with that provision, but I don’t know when.
  • @Catch22: I would recommend posting the query on Fairmark.com forums, where questions are typically answered by tax attorneys and (IRS) enrolled agents. (They provide info and point to IRS publications and rulings; they don't "out" posters.)
  • 1986. Ten year income averaging is still available for qualified plan lump sum distributions to people born before 1936.

    Subtitle E: Miscellaneous Provisions - Repeals income averaging.
    https://www.congress.gov/bill/99th-congress/house-bill/3838

    https://www.rbcwm-usa.com/resources/file-687802.pdf
  • Hi @InformalEconomist Thanks for the reminder. I've viewed Fairmark in the past but had not added the site to my current "to do" list.
    Take care,
    Catch
  • @msf: thanks for doing the legwork and for reminding me how old I am. 1986??
  • I had an investment property sale and my investment advisor did a 1031 to defer taxes. Exchanged to a managed property to free up my time and paid no tax.
  • @RisklessInSeattle
    I know about the use of 1031's; but this transaction is not flipping land into another similar investment.
    Regards,
    Catch
  • One way to "income average" is to literally sell over time. Say 10% each year. If it is income-generating land, then you could get 90% of the revenue when you retained 90% of the ownership and so on.

    That's a little messy. A way to effect something similar is to make the transaction a seller-financed sale and collect installment payments. I would have thought that such a sale would be treated as two separate transactions - a competed sale now, and a mortgage where you are the lender.

    But Congress (IRC § 453) long ago decided that for installment sales, capital gains would not be recognized until payments were made. Since the payments are made over several years, this becomes another way to spread the recognized capital gains over time.

    IRS Topic 705 - Installment Sales
    Form 6252 - Installment Sale Income
    Pub 537 - Installment Sales
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