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LunarEclipse

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One thing nobody has mentioned yet - if you do a cost segregation study and then later convert the property back to a long-term rental, you don't lose the benefits of the cost segregation. The accelerated depreciation schedule stays in place. BUT, be aware that if you sell the property, all that accelerated depreciation will be subject to depreciation recapture at a 25% tax rate (assuming current tax law). So while you get great tax benefits now, you'll potentially pay more when you sell.

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This is really helpful, thanks! Do you know if doing cost segregation affects your basis in the property? And if I only Airbnb one unit of the duplex, can I still do cost segregation on the whole building?

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LunarEclipse

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Cost segregation doesn't change your overall basis in the property - it just changes the timing of when you get to take the depreciation deductions. Your basis will still be reduced by the same total amount over time, you're just front-loading more of the depreciation. For your duplex situation, you can absolutely do cost segregation on the entire building. You'll just need to track the two units separately on your tax return since they'll have different usage (short-term vs. long-term rental). The cost segregation study would typically break this down for you, showing components specific to each unit as well as shared components like the roof, foundation, etc.

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Yara Khalil

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One warning about cost segregation - the IRS has been increasing scrutiny of these studies in recent years. Make sure whoever does yours is legit and has engineering credentials. I've seen people try to DIY this and get absolutely hammered in audits.

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Keisha Brown

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Definitely agree with this! My brother tried to save money by using some online template for cost segregation and got audited. Ended up owing way more plus penalties. Sometimes you really do get what you pay for.

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Dylan Cooper

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@Yara Khalil This is so important to emphasize! I work in tax preparation and see way too many people try to cut corners on cost segregation studies. The IRS specifically looks for certain qualifications - the engineer needs to be licensed and the study needs to follow specific methodologies. A proper study should include detailed engineering analysis, site visits, construction drawings review, and compliance with IRS guidelines. Yes, it costs more upfront, but it s'essentially audit insurance. The savings from accelerated depreciation are only beneficial if they hold up under scrutiny. For anyone considering this strategy, ask potential providers about their audit defense guarantee and make sure they have actual engineering credentials, not just tax credentials.

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Recommendations for software to prepare and e-file 1065s with multiple K-1s for startup investment LLCs

I'm managing two LLCs that were set up as investment vehicles for early-stage startups (basically SPVs). One I've been handling myself for years, but I recently had to take over another one when the management company (Assure) went under and left us hanging. Between these two entities, I'm now responsible for filing multiple 1065s and generating K-1s for around 40-50 members total. Up until now, I've been doing everything manually which has been manageable but tedious for the first LLC since our income and expenses are pretty minimal. The biggest headache is having to re-enter all the member information each year. With two LLCs now, I'm thinking it's finally time to use actual tax software that can hopefully save all this data for future filings. Both LLCs are pretty straightforward from a tax perspective - minimal expenses, occasional income from distributions when a portfolio company gets acquired, etc. I'm not looking for anything super sophisticated, just something that makes the process less painful and can handle batch creating those K-1s efficiently. Has anyone used TurboTax Business, TaxAct, H&R Block Business, or any other software for filing partnership returns with multiple K-1s? Looking for recommendations on what works well specifically for investment LLCs/SPVs. Hoping to find something that makes the process smoother and justifies the cost compared to my manual approach.

StarStrider

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Has anyone used CCH Axcess for SPVs? My CPA recommended it to me for our angel fund, but the pricing seemed outrageous for what's essentially a passive investment vehicle with 25 investors.

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Luca Esposito

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CCH is definitely overkill for what you're describing. It's enterprise-level software designed for accounting firms handling hundreds of complex returns. For a couple of investment LLCs, you'd be paying for a ton of features you'll never use.

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Ava Kim

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For your situation with multiple investment LLCs and 40-50 K-1s, I'd recommend starting with TaxAct Professional as Isabella mentioned. I've been using it for my real estate investment partnerships for 3 years now, and it handles the member data carryover beautifully. The key advantage for investment vehicles is that once you set up the allocation percentages and member information, subsequent years are mostly just updating income/loss amounts and any membership changes. TaxAct's batch K-1 printing and e-filing capabilities will save you hours compared to manual preparation. One tip: when you first set it up, take the time to carefully enter all the member information including addresses and SSNs. The software will catch common errors like mismatched names/SSNs that could cause IRS notices later. For the price point (around $200-300 per return), it's a solid middle ground between DIY manual work and expensive professional software. The learning curve is pretty gentle if you're already familiar with 1065 forms, and their support is responsive when you run into questions about specific partnership allocations.

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Camila Castillo

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Quick warning about cashing old bonds - the bank teller might not know how to handle them properly! When I cashed my old EE bonds, the first bank I went to reported the ENTIRE amount as interest on my 1099-INT, not just the interest portion. It was a huge headache to fix. Make sure whoever cashes them understands the difference between the principal (what you paid for the bond) and the interest (what you earned). The 1099-INT should only show the interest amount.

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This happened to me too! I ended up having to file an amended return because the bank reported it wrong. Such a pain. I recommend going to a larger bank branch where they handle bonds more frequently.

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Zoe Papadakis

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Just to add another perspective here - if you're dealing with multiple old bonds from different years, it might be worth keeping detailed records of when you cash each one. I had EE bonds from 1991, 1992, and 1993 that I found all at once, and when I cashed them in 2023, the bank lumped all the interest together on one 1099-INT. This created some confusion because technically each bond had different interest calculation periods and rates. I ended up having to request separate documentation from the Treasury to show the breakdown for my records. Not a huge deal, but something to be aware of if you're in a similar situation with multiple bond years. Also seconding what others said about those 1992 bonds likely being done earning interest - definitely get them cashed sooner rather than later!

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Pregnant and being told to claim unemployment instead of maternity leave - legal?

So I'm in a bit of a sticky situation with my small business employer (we're a team of 7 people total). I'm currently pregnant and due in December, and my boss just had a conversation with me about my upcoming maternity leave that has me concerned. They're suggesting that instead of providing paid leave, I should file for unemployment and claim that I was laid off due to business slowdown. They said they'd hold my position for me and give me a return-to-work date in February. They mentioned our sales numbers are genuinely down from last year, so there's a "legitimate" reason they could use if unemployment office checks. When I had my first baby in 2023, they initially suggested the same thing. I tried filing but was honest about having a baby and got denied (obviously). They ended up paying me $400 weekly for the 8 weeks I was out instead. This time they're explicitly telling me NOT to mention my pregnancy and just say I was laid off. They're assuring me I "should get paid no problem" and won't have to report job searching activities. I'm really uncomfortable with this. Two mom friends I asked said this sounds like fraud, and when I privately asked my assistant manager, they agreed it seems sketchy. I'm worried about tax implications too - I'll be claiming a newborn on my taxes for the exact period I was supposedly "laid off." My employer has been good to me in many ways, and I don't want to get them in trouble, but I also don't want to commit fraud. I need income during my maternity leave, but this doesn't feel right. Is what they're suggesting legal? Could I get in trouble? Are there other options I should explore?

Dylan Wright

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Omg totally illegal! My sister works for unemployment and she says people get caught doing this ALL THE TIME. They can check hospital records, birth certificates, social media, etc. The system flags cases where someone files taxes with a new dependent born during unemployment claims. Also when u certify for unemployment benefits every week, you have to confirm ur available to work full time. If ur recovering from childbirth/caring for newborn, that's not true. Lying on those certifications is fraud. Penalties are no joke. My cousin got caught doing similar (different situation but same idea of claiming unemployment when not eligible) and had to repay ALL benefits plus a 30% penalty. They also banned her from getting unemployment for 5 years, which really hurt when she actually did lose her job later. Tell ur work NO WAY and start looking into legitimate options like short term disability. Some states have paid family leave too.

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Sofia Torres

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This is so crazy! Can u also report the employer for suggesting this? Seems like they should be in trouble too for telling employees to commit fraud!

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Yuki Sato

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This is definitely unemployment fraud and you should absolutely not do this. I work in tax preparation and see the aftermath of these situations regularly. The IRS and state unemployment offices have sophisticated cross-referencing systems that will catch discrepancies between your unemployment claims and tax filings. When you file your 2025 taxes claiming a newborn dependent born in December, but also received unemployment benefits during that same period for being "laid off," that's going to trigger automatic flags in the system. The timeline will be obvious - you can't be actively seeking work while in the hospital giving birth and caring for a newborn. Beyond the fraud issue, there are legitimate options you should explore first. Many people don't realize that short-term disability insurance often covers pregnancy and childbirth recovery. Check your employee benefits package - you might already have this coverage. Also, some states have temporary disability insurance programs that provide partial wage replacement during recovery from childbirth. If your employer is genuinely experiencing financial hardship and can't provide paid leave, they should be honest about that rather than suggesting illegal workarounds. There may be legitimate ways to structure unpaid leave with partial income replacement through proper channels. Document everything about these conversations and consult with an employment attorney if needed. Your employer putting you in this position is problematic on multiple levels.

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Can the IRS legally seize my tax refund due to limitations on claims for refund?

I'm in a really frustrating situation with the IRS and could use some advice. For various personal reasons, I filed my 2016-2020 tax returns late (in 2021). Here's where things get messed up - I had about $75,000 sitting "on account" with the IRS that I was trying to apply toward my 2017 tax liability. Just got hit with a CP45 notice saying: "Your 2016 Form 1040 shows you wanted $75,000.00 of your overpayment applied to your 2017 estimated tax. We couldn't apply any of the overpayment as your requested because the period for claiming an overpayment appears to have expired before we received your return." Now I'm getting hammered with late filing and payment penalties for 2017, which I understand, but they're calculating those fees WITHOUT applying the $75K I had sitting with them. It's like the money just vanished into thin air! I've been digging through IRS documentation and found the statute of limitations on claims for refund, but this doesn't make sense to me. This isn't some store credit or airline miles expiring - this is actual money I paid to the government! I always thought letting the IRS hold onto my money was the responsible thing to do rather than requesting refunds. Whenever I had overpayments, I'd just tell them to keep it "on account" for future tax years or in case I underpaid something. I've had a couple conversations with IRS agents about this already. They basically told me they've "seized" the money and won't apply it to any tax year because of the statute of limitations. They just told me to wait for the official notice, which I now have. Is this even constitutional? Doesn't the Fourth Amendment protect against unreasonable seizures? How can they just make $75K of my money disappear? Is there any way to fight this or get my money back?

Aiden O'Connor

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Just to add a potentially useful resource - publication 556 "Examination of Returns, Appeal Rights, and Claims for Refund" has detailed information about the limitations on refund claims. The key section for your case would be the "Time for Filing a Claim for Refund" portion. Also look into "protective claims" which are sometimes allowed even after limitations periods have passed if there were special circumstances. Not sure if your situation qualifies, but worth investigating. If you filed during COVID, there were also special extensions to some filing deadlines that might potentially apply to your situation. The IRS issued several notices extending various deadlines.

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Sienna Gomez

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Thank you for these suggestions. I'll definitely look into publication 556 and the protective claims option. My filing in 2021 was during COVID, so I'll also research if any of those special provisions might apply to my situation. Do you think it would be worth hiring a tax attorney for a $75K issue like this? Or should I try working through IRS channels first?

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Aiden O'Connor

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For $75K, I would absolutely consult with a tax attorney who specializes in IRS disputes - many offer free initial consultations. Try to find someone who has specific experience with statute of limitations issues and refund claims. You should simultaneously pursue IRS channels since there are strict time limits on certain appeals. Start with a formal written request for reconsideration that clearly lays out why you believe the statute of limitations shouldn't apply in your case. Be extremely specific about timelines, payment designations, and any COVID-related provisions that might apply. The Taxpayer Advocate Service can also be extremely helpful as a third option - they're designed to help with exactly these kinds of issues where standard IRS procedures have resulted in unfair outcomes.

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Dmitry Popov

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I'm really sorry you're going through this - $75K is an enormous amount to lose to a technicality. While the statute of limitations rules are unfortunately strict, there might be some avenues worth exploring given the amount involved. One thing that stands out to me is that you consistently elected to keep overpayments with the IRS rather than taking refunds - this shows a clear pattern of intending to maintain credit balances for future tax obligations. Some courts have distinguished between different types of payments and credits in similar cases. Have you looked into whether any of the COVID-related relief provisions might apply to your timeline? The IRS issued numerous deadline extensions and special procedures during 2020-2021 that could potentially affect limitation periods. Also, consider whether there were any IRS processing delays or errors that contributed to this situation. If you can document that the IRS failed to properly process your returns or apply your payments in a timely manner, that might provide grounds for an exception. Given the amount involved, I'd strongly recommend consulting with a tax attorney who specializes in statute of limitations cases before accepting this outcome. Many offer free consultations and could quickly assess whether you have viable options for recovery. Don't give up yet - $75K is worth fighting for, and there are specialized advocates who deal with exactly these types of IRS disputes.

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