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Tax implications of selling a small business after 34 years - Capital Gains question

Hi everyone! My uncle has been running a diner in Michigan for 34 years. He purchased it back in 1990 for about $65k when it was just a small coffee shop. Over the years, he invested roughly $270k in renovations to expand it into a full-service diner with a larger dining area and updated kitchen. Most of these improvements were done around 2008-2013. He's looking to retire now and has a buyer willing to pay $675k for the business. His accountant just told him he'll need to pay approximately $135k in capital gains taxes on the sale. This seems absolutely outrageous to both of us! That's like a 40% tax rate on his profit when you do the math. When you factor in inflation, those original investments would be worth way more in today's dollars. He's basically getting penalized for building a successful small business through decades of hard work. His annual income from the diner has averaged about $75k over the years. His accountant mentioned something about "depreciation recapture" being the reason for the high tax bill, but that makes little sense to us. The renovations aren't in terrible condition - the dining area still looks nice and the kitchen equipment works well. This sale represents the majority of his retirement savings. Can anyone explain why the tax hit is so massive on a small business he's owned for over three decades? Does this seem right to everyone else? Update: Thanks for all the explanations about depreciation recapture and how it affects capital gains. My uncle and I understand the situation much better now. He's calmed down considerably after learning that the tax breaks he received while running the business are connected to the taxes due upon selling.

One thing nobody's mentioned - your uncle should check if his state offers any small business retirement or transfer tax incentives. Here in Pennsylvania, we have programs that provide tax breaks for long-term business owners selling for retirement. Also, make sure his accountant is considering his basis correctly. The $65k purchase price plus documented improvements of $270k should both count toward his basis. Sometimes accountants miss some of the capital improvements if they weren't all properly categorized over the years. And definitely get a second opinion! I got three different tax estimates when selling my landscaping business, with the amounts varying by over $40k between professionals.

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Lia Quinn

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This is so true! When I sold my bakery last year, the first accountant completely overlooked some leasehold improvements we made in 2013. Getting a second opinion saved me about $18k in taxes. Different tax pros can interpret the rules very differently, especially for small businesses with decades of history.

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KaiEsmeralda

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Your uncle's situation is unfortunately very common with long-term small business owners. That $135k tax bill on a $675k sale actually breaks down to roughly 20% effective rate, which isn't as outrageous as it first appears when you understand the components. The key issue is that over 34 years, your uncle likely claimed hundreds of thousands in depreciation deductions on his tax returns - both on the original building/equipment and all those renovations. Every year he owned the business, these deductions reduced his taxable income, saving him money at his then-current tax rates. Now the IRS wants those tax savings back through "depreciation recapture" at 25%, plus regular capital gains tax (15-20%) on any remaining profit. It's not a penalty - it's the government collecting on tax benefits he received over three decades. A few suggestions: 1) Verify his accountant calculated the basis correctly (original $65k + documented $270k improvements should total $335k basis), 2) Consider if any improvements qualify for different depreciation schedules, 3) Explore installment sale options to spread the tax over multiple years, and 4) Definitely get a second opinion from a CPA who specializes in business sales. The silver lining is that without those annual depreciation deductions, his taxes would have been much higher every year he operated the diner.

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I had this exact issue on February 8th, 2023. My DDD was 02/08/2023, SBTPG had taken their fees, and I had a trace number, but no deposit hit my account. After calling Wells Fargo on February 10th, 2023, they confirmed no pending deposits had been rejected. I then called SBTPG on February 13th, 2023, and after escalating to a supervisor, they discovered the ACH transfer had failed due to a system error on their end. They reprocessed it that same day, and I received my funds on February 15th, 2023. The key was getting to a supervisor at SBTPG who could actually see the failed transfer details and manually reprocess it.

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This is such a common issue this tax season! I went through something similar with SBTPG and Bank of America last month. The trace number is actually a good sign - it means the IRS has successfully transmitted your cousin's refund to SBTPG. What I learned from my experience is that there's often a disconnect between SBTPG's systems and the receiving bank's processing timeline. In my case, Wells Fargo was holding the deposit for additional verification due to the third-party processor routing, which added 4 extra business days beyond the DDD. I'd recommend your cousin call Wells Fargo first to ask specifically about any pending ACH transfers from SBTPG or TPG - sometimes the bank can see pending deposits that haven't been released yet. If Wells Fargo shows nothing, then definitely escalate with SBTPG using that trace number as reference. The key is being persistent and asking for supervisors who can access the detailed transfer logs.

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Aiden Chen

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Quick question - I'm facing a similar issue with my leased F-250 - does anyone know if TaxAct has a specific section for handling lease inclusion amounts for heavy vehicles? I can't seem to find it anywhere in the business vehicle section.

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Zoey Bianchi

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In TaxAct's business section, after you enter the vehicle info and specify it's leased, there should be a screen that asks about "actual expenses" - that's where you'll enter your lease payments. Then it should automatically prompt you about the inclusion amount based on the vehicle value and weight class you entered. At least that's how it worked for me last year with my Silverado 2500.

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Just went through this exact same situation with my leased Ram 2500 last month! The key thing that helped me was realizing that in TaxAct, when you're in the vehicle section, you need to make sure you select "leased" rather than "owned" early in the process. Once you do that, it should give you the option to deduct actual expenses (your lease payments) rather than forcing you into depreciation calculations. If it's still asking for depreciation methods after you've indicated it's leased, try going back to the vehicle type selection and make sure it's properly categorized as a business lease. The software sometimes gets confused if you accidentally indicate mixed personal/business use or if the initial setup wasn't clear about the lease vs purchase distinction. For the inclusion amount that others mentioned - TaxAct should calculate this automatically once you've entered the vehicle's fair market value and lease terms correctly. You shouldn't have to do any manual calculations for that part.

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This is exactly what I needed to hear! I think I may have messed up that initial selection between leased vs owned. I'm going to go back and double-check that I properly indicated it's a business lease from the beginning. It sounds like once that's set correctly, TaxAct should handle most of the complex calculations automatically. Thanks for the step-by-step guidance - it's so helpful to hear from someone who just went through this same process!

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Is anyone else annoyed at how confusing our tax system is? Like why do we need so many different forms? In other countries the government just sends you a statement with everything already calculated and you just verify it!

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For real! My brother lives in Norway and they literally just text him when his "tax return" is ready to review. Takes him 5 minutes to check and confirm. Meanwhile I'm drowning in forms and freaking out about missing something important.

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Liam Brown

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I totally get the confusion! This is actually one of the most common tax questions new filers have. Just to add to what others have said - think of it this way: your W-2 is like a receipt showing what you earned and what taxes were already taken out of your paychecks. The 1040 is like your final tax calculation where you figure out if you owe more money or if you get a refund. The good news is you did everything right! When you "submitted online," you were filing your 1040 tax return (which used the info from your W-2). The physical 1040 copy is just for your records - definitely keep it safe for at least 3 years like others mentioned. And don't worry about feeling confused - even people who've been filing taxes for years sometimes mix up the terminology. The important thing is your taxes are filed correctly!

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Does anyone know if you need to amend previous tax returns to claim the FFCRA credit? The notice I got wasn't clear about the process - it just directs me to that Adesso360 portal but doesn't explain if this affects my already-filed returns.

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Liam Cortez

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From what I understand, most FFCRA credits for employers were claimed on quarterly employment tax returns (Form 941) rather than annual income tax returns. If you missed claiming them on your original 941 forms, you typically file Form 941-X to amend those quarterly returns. The Adesso360 portal might be handling the amendment process for you in a streamlined way, but you should definitely verify this with the IRS directly before proceeding.

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Liam Duke

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I was in a similar situation and found that the best approach is to cross-reference multiple sources before taking any action. When I got my FFCRA notice, I first checked if the sender address matched official IRS correspondence (it should come from the Department of Treasury, not a third-party company directly). The timing issue that others mentioned is actually not that unusual - the IRS has been doing targeted outreach to employers who may have missed claiming these credits during the original periods. They're using third-party contractors like Adesso360 to help process the backlog of potential claims. However, I'd strongly recommend never clicking links in the letter or going directly to any portal mentioned. Instead, go to IRS.gov and search for "FFCRA tax credit" to find the official information and legitimate pathways to claim any credits you're entitled to. If you determine you do qualify, you can work through official IRS channels rather than risking your personal information with a potentially compromised portal. The peace of mind from verifying through official channels is worth the extra time, especially when dealing with something as sensitive as tax information.

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This is really solid advice! I made the mistake of almost clicking the link in my letter before doing any research. Going directly to IRS.gov is definitely the safest approach. I'm curious though - when you searched for "FFCRA tax credit" on the official IRS site, did you find clear instructions on how to verify if a notice like this is legitimate? I've been having trouble navigating their website to find specific information about these retroactive credit notices and how to tell the real ones from scams. Also, did you end up qualifying for any credits after going through the official channels? I'm still trying to figure out if I even had employees during the qualifying periods that would make me eligible.

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