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One approach that might be worth exploring is a private annuity arrangement, where your mother transfers her shares to you and your sister in exchange for unsecured lifetime payments. This can be particularly effective if she's in good health and expects to live well beyond the actuarial life expectancy. The key advantages are that the transferred shares (and all future appreciation) are immediately removed from her estate, while she receives guaranteed income for life. The payments you make are not deductible, but they're not considered gifts either - they're simply fulfilling the annuity obligation. The payment amount is calculated using IRS actuarial tables based on her age, which often results in payments that are lower than what you might negotiate in a standard installment sale. If she lives longer than the actuarial expectation, you'll pay more than the shares were worth, but if not, you could end up paying less. This strategy works particularly well when combined with life insurance on your mother - the insurance can provide funds to complete any remaining payments to her estate while giving you peace of mind about the arrangement. Just make sure to have a qualified business valuation done to establish fair market value for the shares at the time of transfer.
The private annuity approach is interesting, but I'm wondering about the risk factors involved. What happens if our business experiences a significant downturn and we can't make the annuity payments? Unlike an installment sale where we might be able to renegotiate terms with family, an annuity creates a fixed obligation regardless of business performance. Also, I'm curious about the valuation aspect - since private annuity payments are based on the current fair market value of the shares, wouldn't we want to time this strategy when the business valuation is at a relatively low point to minimize the ongoing payment obligations? Are there any restrictions on when the valuation can be done, or strategies to optimize the timing? The life insurance component makes a lot of sense from a risk management perspective. Do you typically structure that as term or permanent insurance, and who owns the policy - the business or the individual buyers?
You raise excellent risk management questions about private annuities. The inability to renegotiate payments is indeed a major drawback - if your business hits a rough patch, you're still obligated to make those payments from personal assets if necessary. This is why many families prefer installment sales with family members, where there's more flexibility to adjust terms if circumstances change. Regarding valuation timing, you're absolutely right that timing matters significantly. The annuity payments are locked in based on the valuation date, so executing the transaction during a temporary business downturn (maybe after a bad year or during an industry slump) can result in substantially lower ongoing obligations. There aren't specific IRS restrictions on timing, but the valuation needs to reflect fair market value as of the transfer date. For the life insurance, I typically see term insurance owned personally by the buyers (you and your sister) rather than the business, especially in an S Corp where life insurance proceeds could create tax complications. The coverage amount should equal the present value of remaining annuity payments. Some families use decreasing term policies that reduce in coverage as the statistical likelihood of remaining payments decreases over time. The key is running detailed cash flow projections under various business performance scenarios before committing to this structure.
One consideration that hasn't been mentioned yet is the potential impact of the Tax Cuts and Jobs Act provisions that are set to expire after 2025. The current doubled estate and gift tax exemption ($12.92 million per person in 2023) is scheduled to sunset, which could significantly affect some of the advanced planning strategies discussed here. If your mother has substantial other assets beyond the S Corp shares, it might make sense to accelerate some gifting strategies before the exemption potentially drops back to around $6 million per person. This could influence whether you pursue approaches like the family limited partnership or IDGT strategies that rely on gift tax exemptions. Also, have you considered the impact of your state's tax laws? Some states have no capital gains tax, while others impose significant additional taxes on the sale of business interests. If your mother is considering relocating for retirement, the timing of the share transfer relative to any move could affect the overall tax efficiency. The key is to coordinate the business succession planning with broader estate and income tax planning to optimize the outcome for your entire family situation, not just the business transfer itself.
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This is exactly the kind of update we all love to see! That 571 code is such a game changer after being stuck with an 810 freeze for 6+ months. I've been lurking in this community for a while watching everyone's journeys, and your timeline gives me hope for my own situation. What really stands out to me is how quickly your 570 and 571 codes appeared - just one week apart! That suggests once the IRS actually got to reviewing your case, they were able to resolve whatever was flagging it pretty efficiently. From all the stories I've read here, that's usually a really good sign for getting your refund processed soon. The consensus seems to be 1-2 weeks after the 571 for the 846 code to appear, especially with your cycle ending in 05. Definitely keep checking Friday mornings when those weekly transcripts update! After waiting since March, you're finally in the home stretch. Thanks for sharing your detailed timeline - it really helps those of us still waiting to know what to look for. Please keep us updated when you see that 846 code! 🤞
This community has been such a lifeline! I've been reading everyone's experiences for months and finally having my own 571 code feels surreal. The one week turnaround from 570 to 571 definitely gives me hope that they resolved whatever was flagging my return pretty quickly. I'm really crossing my fingers that the 1-2 week timeline holds true - will definitely be checking Friday morning religiously now! It's amazing how much more manageable this whole process feels when you have real people sharing their actual experiences instead of just trying to decode IRS jargon online. Will absolutely update everyone when I see that 846 code! 🙏
Hey Yara! This is such encouraging news after your incredibly long wait! I've been following similar cases in this community and that 571 code is exactly what you want to see after being stuck with an 810 freeze since March. What really stands out about your situation is how quickly things moved once the IRS actually got to your case - going from 570 to 571 in just one week is actually a really positive sign. It suggests they were able to resolve whatever was flagging your return pretty efficiently once they started the review process. Based on what I've seen from others who've shared their timelines here, you're typically looking at 1-2 weeks after the 571 code appears before you see the 846 (refund issued) code. Since yours posted on 09/30 and your cycle ends in 05, definitely keep checking Friday mornings when those weekly transcripts usually update. After waiting 6+ months, you're finally in the home stretch! The hardest part is behind you now. Really hoping you see that 846 code and DDD soon. Please keep us posted - this whole community will be celebrating with you when that refund finally hits your account! 🙌
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Just be careful! A friend of mine tried to deduct the difference between flying and driving for a similar situation, and it triggered an audit. The IRS disallowed the deduction because they determined the primary purpose of the trip was personal (family event). They said personal trips with some business activities don't qualify for travel deductions.
That's not universally true though. The rules are more nuanced. If the primary purpose is business, you can deduct business expenses even if you include some personal time. Your friend's situation might have had other issues or lacked proper documentation.
The key distinction here is that you're not just adding some business activities to a personal trip - you're being forced to change your entire travel method specifically because of business equipment requirements. This creates a stronger case for deducting the incremental costs. I'd recommend documenting everything thoroughly: get quotes for what flights would have cost, keep all driving-related receipts (gas, hotels, meals during travel), and most importantly, document why the equipment was essential and couldn't be shipped or transported any other way. Client emails or contracts showing the equipment requirements would be valuable supporting evidence. One thing to consider is whether you could potentially ship the equipment separately and still fly yourself. If shipping isn't viable due to timing, fragility, or cost, make sure to document why. This helps establish that driving was truly the only reasonable business option, not just a preference. The IRS generally allows deductions for additional costs incurred solely due to business necessity, but they'll want to see clear evidence that the extra expense was unavoidable for legitimate business reasons.
This is really helpful advice! The documentation angle makes a lot of sense. I'm curious though - if the equipment is something that could theoretically be rented at the destination, does that weaken the case for driving being the only option? Like if there's a rental company 200 miles from the wedding location that has similar equipment, would the IRS expect you to explore that instead of hauling your own gear?
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If you sold for $21,500 and bought for $12,000, don't forget that's a $9,500 profit which is subject to capital gains tax! Since you held it more than a year, you'll get the lower long-term rate (0%, 15%, or 20% depending on your income) instead of your regular income tax rate.
It's also worth mentioning that if you had a loss instead of a gain on the land sale, you can deduct that too. A friend of mine had to sell some land at a loss due to financial hardship, and he was able to offset some of his other income with the capital loss. There's a limit of $3,000 per year for capital losses against ordinary income, with the rest carrying forward to future years.
One thing that hasn't been mentioned yet is the Net Investment Income Tax (NIIT). If your modified adjusted gross income exceeds certain thresholds ($200,000 for single filers, $250,000 for married filing jointly), you may owe an additional 3.8% tax on your capital gains from the land sale. This is separate from the regular capital gains tax and catches a lot of people off guard. The good news is that with a $9,500 gain, it's unlikely to push most people over those income thresholds unless they already have substantial other income. But it's something to be aware of when planning your tax strategy, especially if you're considering selling other investments in the same year. Cash App Tax should automatically calculate this if it applies to your situation, but it's worth understanding so you're not surprised by an unexpected tax bill.
That's a really helpful point about the NIIT! I'm nowhere near those income thresholds, but it's good to know about for the future. Quick question - does the 3.8% apply to the entire gain or just the portion that pushes you over the threshold? And are there any other "surprise" taxes on capital gains that people should be aware of when selling land?
Freya Johansen
Don't forget to check your state return too! If you're amending federal for a missed 1099-R, you might need to amend state as well, even for non-taxable events. Some states require reporting of all 1099-Rs regardless of taxability.
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Omar Fawzi
•Good point. Every state has different requirements. For example, I live in California and they want you to report all retirement transactions even if they're non-taxable federally.
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Simon White
Great question! Just went through this exact process last month with a missed 1099-R for a Roth conversion. You only need to sign the 1040X form - that's the official amendment document. The revised 1040 is just supporting documentation to show what the corrected return looks like. One tip I wish I'd known earlier: make sure to include a brief explanation letter with your amendment explaining that this was a non-taxable Roth rollover that was simply omitted from the original filing. This helps the IRS processor understand the context and can speed up processing. Also double-check that you're reporting the rollover in the correct section of your 1040 - it should go in the IRA distributions section with the taxable portion marked as $0. The IRS gets confused when the reporting doesn't match their records from the 1099-R. Your amendment should be straightforward since there's no tax impact, but getting all the documentation right upfront will save you potential follow-up letters from the IRS.
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Malik Jenkins
•This is really helpful advice! I'm actually dealing with a similar situation right now. Quick question - when you mention including an explanation letter, is there a specific format the IRS prefers, or can it just be a simple note explaining the oversight? Also, did you send everything via regular mail or did you use certified mail to make sure they received it? I'm a bit paranoid about my amendment getting lost in the mail since I've heard horror stories about IRS processing delays. Want to make sure I cover all my bases like you did!
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