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I went down this rabbit hole last year when selling my business. Here's what my accountant (who doesn't sell either product) told me: monetized installment sales are specifically what the IRS targeted with Notice 2022-21, while DSTs are technically different but still high-risk. The key difference is that in a monetized installment sale, you're selling directly to the end buyer but getting a separate loan from a lender. In a DST, you're selling to a trust that then sells to the end buyer. The DST adds an extra layer that might avoid the specific issues in the IRS notice, but creates its own potential problems. He ultimately advised me against both and suggested a 1031 exchange into rental properties combined with opportunity zone investments for the portion that couldn't be exchanged. Ended up being less risky and actually gives me ongoing income.

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Juan Moreno

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But don't you lose flexibility with a 1031? I want to invest the proceeds in my new business venture, not just more real estate. Did your accountant discuss that limitation?

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That's absolutely correct - 1031 exchanges definitely lock you into real estate investments, which was fine for my situation since I wanted passive income. For business investments, it wouldn't work. For investing in a new business venture, you might want to look into Qualified Small Business Stock (Section 1202) if you're setting up a C-Corp, or potentially an installment sale with a longer genuine payment period (without the monetization aspect that triggers IRS concerns). Both have limitations but might be less risky than DSTs or monetized installment sales. The right strategy really depends on your specific goals and risk tolerance.

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Amy Fleming

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Has anyone actually used either of these structures successfully? All I see online are promoters selling them or people warning against them, but never anybody who's actually done it and can speak to their experience several years later (after potential IRS audits).

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Alice Pierce

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I know someone who did a DST about 6 years ago. They're still getting payments from the trust and haven't been audited...yet. But they're constantly worried about it, especially with the increased IRS funding. Not sure the stress is worth it honestly.

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Need advice: Amending last year's tax return before filing this year's joint return?

I'm in a bit of a bind that Google hasn't been great at solving, so I'm turning to you folks for some advice! My husband and I filed separately for our 2023 taxes. We messed up by reporting our mortgage balance incorrectly, which led us to deduct less interest than we should have. Because of this error, we took the standard deduction instead of itemizing, which wasn't the best move financially for us. We only caught this mistake while preparing our 2024 returns. We're planning to amend our 2023 returns to fix the mortgage interest issue and switch from standard to itemized deductions for that year. But here's the tricky part - for 2024, we want to file jointly. On the 2024 tax worksheets, there's a question asking whether we took standard deduction or itemized last year. This is where I'm confused. Should we: 1. File the amendment for 2023 first, wait for the IRS to process and accept it, and then file our 2024 joint return (probably with an extension since this could take months)? 2. Go ahead and file our 2024 return now and answer the question as if our amendment was already accepted (saying we itemized last year, even though the official record currently shows standard deduction)? 3. File our 2024 return now saying we took standard deduction (what's currently on record), then potentially have to amend our 2024 return later? If we go with option 3, would we need to amend this year's return next year for any reason? This timing issue is giving me a headache! Thanks in advance for any guidance!

StarSurfer

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Everyone is overlooking something important here - the timing could matter depending on what state you live in! Some states require your federal return to be fully processed before you can file state returns accurately. In California for example, if your federal amendment changes your AGI significantly, you'll need to amend your state return too. And filing your new year's state return with inconsistent prior year info can trigger automatic review. Before you decide, check your state's requirements for amendments and how they handle prior year references on current returns.

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Mei Zhang

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That's a great point I hadn't considered. We're in Michigan, and I'm not sure how strict they are about this. Do you know if Michigan has specific requirements about the timing of federal amendments and their impact on current year state returns?

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StarSurfer

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Michigan is actually less strict than some states about this. They don't automatically require state amendments just because you amended federal (though you should if the changes affect Michigan taxable income). For your situation, Michigan won't flag your current return based on the prior year deduction method question alone. However, if your mortgage interest deduction relates to a Michigan property and affects your Michigan property tax credit, you'll want to make sure both years are consistent. I still recommend filing the amendment first or simultaneously with your current return, but Michigan isn't one of the states that will automatically reject or flag your current return over this specific issue.

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Ava Martinez

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I work at a tax firm and we handle this exact situation regularly. Here's what most preparers don't tell you: the IRS systems don't actually cross-reference your answer about last year's deduction method with their records before processing your current return. File your 2023 amendment and 2024 return simultaneously. On your 2024 return, answer according to what WILL be true after amendment (that you itemized in 2023). Keep a detailed note with your tax records explaining the situation and timing. In the extremely unlikely event you're ever questioned, this note shows you were being forthright and not attempting to misrepresent anything. What tax software are you using for 2024? Some handle this situation better than others.

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Not OP but curious - is there any difference in how the major tax software packages handle amendments? I've been using TurboTax for years but their amendment process seems clunky.

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Sofia Torres

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One thing nobody's mentioned - check if you accidentally claimed any credits you're not eligible for. I once got a surprisingly high refund because my tax software somehow checked the box for the American Opportunity Credit even though I wasn't in school that year. Small software glitches can make a huge difference!

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That's a good point! I'll double check all the credits. I don't think I should qualify for education credits since I haven't been in school for a few years, but maybe something got checked accidentally. I didn't get any unusual questions about education expenses though. Is there a way to see a summary of which credits and deductions were applied on my return? I'm using TaxSlayer if that helps.

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Sofia Torres

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In TaxSlayer, you should be able to view a summary of your return before filing. Look for the "Review" or "Summary" section, which typically shows all the credits and deductions that were applied. Pay special attention to any refundable credits like EITC, American Opportunity Credit, or Child Tax Credit. You can also look at the actual tax forms that are generated - specifically check Schedule 3 and Form 1040 to see which lines have amounts that might be surprising. If you see amounts on lines for credits you don't think you qualify for, that's a red flag.

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Has anyone actually confirmed if tax software can make calculation errors? Like actual math errors? I always thought it was user input errors but now I'm paranoid about my own return.

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Tax software rarely makes actual calculation errors - they're pretty rigorously tested. It's almost always user input errors. The most common mistakes I see (I help friends with taxes) are: 1. Entering the same income twice 2. Mixing up which numbers go in which fields (like the withholding error OP probably made) 3. Missing a form entirely 4. Clicking yes/no incorrectly on a qualifying question

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Thanks for clarifying. That makes me feel better about my return. I was starting to wonder if I needed to redo everything in another software just to double check the calculations!

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Eve Freeman

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Don't overlook state estate taxes too! Federal estate tax has a high exemption amount ($12.92 million for 2023), but some states have much lower thresholds. I learned this the hard way with my mother's estate - we were under the federal limit but got hit with a state estate tax bill we weren't expecting.

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Good point - what states have their own estate taxes? We're in Michigan if that matters.

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Eve Freeman

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As of 2023, twelve states plus DC have estate taxes: Connecticut, Hawaii, Illinois, Maine, Maryland, Massachusetts, Minnesota, New York, Oregon, Rhode Island, Vermont, Washington, and the District of Columbia. Michigan doesn't have a state estate tax, so you're fortunate there! The exemption thresholds vary widely - Massachusetts and Oregon have exemptions as low as $1 million, while states like Hawaii align more closely with the federal exemption. If your stepdad owned property in any of these states, you might still need to file a state estate tax return, even if most assets were in Michigan.

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Consider opening a separate bank account for the estate using that EIN. It helps keep the estate finances completely separate and makes accounting much easier. We made the mistake of trying to track estate expenses through my mom's personal account after dad died, and it created a huge mess at tax time.

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Caden Turner

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100% agree with this. When my husband died, having a separate estate account made everything so much clearer. Also made it easier to show the court during probate that I was handling things properly.

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That's really helpful advice! I'll talk to mom about setting up a dedicated account with the EIN. Better to keep things organized from the start than trying to untangle them later.

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Just wanted to add that there are income limits for the AOTC too! The credit starts phasing out if your MAGI is above $80,000 ($160,000 for joint filers) and completely phases out at $90,000 ($180,000 for joint filers). Since your sister only makes around $14,300, she should qualify for the full amount assuming she meets the other requirements. Also make sure she's eligible - she needs to be pursuing a degree, enrolled at least half-time, not have completed the first four years of higher education, and not have claimed the AOTC for more than four tax years. And double-check she has a valid SSN by the due date of the return!

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Liam Duke

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Thanks for mentioning this! She definitely meets all those requirements - she's a sophomore working on her bachelor's degree and this will be her second time claiming the AOTC. Her school sent a 1098-T showing about $9,500 in qualified tuition and expenses, so I think we're good on that front. I was just really confused about how much of it she could actually get back as a refund since her tax liability is only around $300 after her standard deduction.

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Based on what you've shared, your sister should receive the full benefit of the AOTC. The $300 tax liability will be completely eliminated by the non-refundable portion of the credit, and she'll get the full $1,000 refundable portion back as a refund. With $9,500 in qualified expenses, she qualifies for the maximum $2,500 AOTC (calculated as 100% of the first $2,000 in expenses plus 25% of the next $2,000). It's great that she's maintaining her education while working - this credit is specifically designed to help students in her situation!

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Demi Hall

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don't forget that the expenses have to be for 2024 tax year! i messed up last year by including some expenses that were actually for the spring semester 2023 that i paid in december 2022. the 1098-T can be confusing because sometimes schools report amounts billed versus amounts paid. check box 1 and box 2 carefully!!

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This is so important! My daughter's school reports in Box 2 (amounts billed) rather than Box 1 (payments received). We had to adjust what was on the 1098-T to reflect when payments were actually made. The rule is you claim the AOTC in the year you make the payment, not when you're billed or when classes are taken.

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