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Facing $40k+ in tax problems - would fixing retroactive payroll for S corp be cheaper?

I'm trying to get a rough idea of how much it'll cost me to file 3.5 years of retroactive payroll for my S corp. This whole situation is a complete nightmare and I'm stressing hard about it. Here's the mess I'm in: Back in 2020, my CPA recommended I could save money by making an S election for my LLC. We proceeded with that plan - for my 2020 taxes. The 1120S he filed had the S election box checked and listed 1/1/2020 as the effective date. I filed my 2021 and 2022 personal and business taxes without any issues - everything seemed fine. (Haven't filed 2023 yet - got an extension.) Well, after not getting my expected corporate tax refund, I called the IRS to check on it. That's when I discovered: 1. My CPA never actually filed Form 2553 (Election by a Small Business Corporation) 2. The IRS has zero record of my corporation because there was no 2553 filed 3. The IRS apparently has no record of any corporate tax returns being filed - seems like without the 2553 to match them to, they just vanished somewhere?? I had NO CLUE about this problem - every year I'd get confirmation that my taxes were e-filed successfully. I have copies of all the filings. Never got any letters or notices from the IRS. Nothing indicated there was an issue. Now I'm looking at two options: Option 1: Amend my taxes to reflect my business as the single-member LLC (Schedule C) that I apparently still am according to the IRS, despite thinking I was an S corp for the last 3.5 years. Option 2: Try to fix the S corp election issue and file retroactive payroll...

Gabriel Ruiz

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Don't forget about state tax implications too! I went through something similar in California and while I was fixing the federal issues, I completely missed that I also needed to address the state filings. Ended up with a whole second headache. Make sure whatever solution you choose, you're addressing both federal AND state requirements. Each state has different rules about conforming to federal S-corp elections.

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Rajan Walker

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Oh man, I hadn't even thought about the state implications. I'm in Illinois - do you know if they automatically recognize the federal S-corp election or do I need to file something separate with them too?

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Gabriel Ruiz

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Illinois does generally conform to federal S-corp elections, but they still require their own notification. You need to file Form IL-1120-ST with the Illinois Department of Revenue, and they technically want you to submit this within 60 days of your federal election. Since your federal election is going to be retroactive, you should contact the Illinois Department of Revenue specifically about your situation. They may require you to file a separate late election acceptance for state purposes. Unlike some states that automatically accept the federal election, Illinois wants to be formally notified, even though they typically follow the federal tax treatment.

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Make sure to get a new CPA! I had a similar situation where my accountant messed up my S-corp election. I went through 3 different accountants before finding someone who actually knew how to handle the correction properly. Look for someone who specifically has experience with entity election corrections and IRS abatement requests. A good CPA will know exactly what documentation to prepare and what procedures to follow for your specific situation.

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Any recommendations for finding a CPA who specializes in fixing these kinds of messes? I've been looking but everyone I talk to seems to have a different opinion on how to handle it.

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Amina Toure

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I'd recommend looking for CPAs who are enrolled agents (EAs) or who specifically advertise IRS representation services. You can search the IRS directory for enrolled agents in your area. Also check with your state CPA society - they often have referral services where you can specify you need someone with experience in entity election corrections. When you interview potential CPAs, ask specifically about their experience with Revenue Procedure 2013-30 late S-corp elections and penalty abatement requests. A good one should be able to explain the process clearly and give you a realistic timeline and cost estimate. Don't go with anyone who guarantees a specific outcome - the IRS has discretion in these cases.

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Ally Tailer

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Just FYI - if you're a frequent gambler, you should keep a gambling diary or log for ALL your gambling activities (wins AND losses). Document dates, locations, type of gambling, amounts, witnesses if possible. The IRS allows you to deduct losses up to the amount of your winnings, but only if you itemize deductions AND have proof of those losses. Without documentation, you can't claim the losses but still have to report all the winnings.

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Simon White

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Thanks for this tip! Do casino loyalty cards help with tracking for tax purposes? I always use mine when I gamble.

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Ally Tailer

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Casino loyalty cards can definitely help as supporting evidence, especially at casinos that provide win/loss statements at year-end based on your card usage. However, these statements aren't considered complete documentation by themselves since they only track play when your card is inserted. For complete documentation, you should still maintain your own gambling diary with dates, locations, and specific session results. The IRS wants to see contemporary records created at or near the time of gambling. Your personal log combined with loyalty card statements provides much stronger documentation if you're ever audited.

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One thing nobody mentioned - even if you get a W-2G with taxes already withheld, the amount withheld is usually only 24% (federal backup withholding rate). If you're in a higher tax bracket, you might still owe more when you file! Had this happen to me last year with a $15k slot win. Was shocked when I still owed another $1,700 at tax time even though they'd already withheld like $3,600!

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Yep, happened to me too! Plus some states require state income tax that isn't withheld on the W-2G, so you might get hit with that too.

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This is such an important point that catches so many people off guard! The 24% withholding is really just a flat rate that doesn't account for your actual tax situation. If you're in the 32% or 35% bracket, or if you have other income that pushes you into a higher bracket, that withholding won't be nearly enough. It's definitely smart to set aside some of those winnings for the potential tax bill come April!

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For what it's worth, I've been filing my own 5500-EZ for my solo 401k for the past 3 years. It was intimidating at first, but it's actually not that complicated if your situation is straightforward. The key things: 1. If your plan assets are under $250k at the end of the year, you might be exempt from filing 2. Make sure you know your plan number and EIN 3. The instructions on the IRS website are actually decent once you read through them carefully 4. File by July 31 for calendar-year plans I spend maybe an hour each year on this now. Just my experience, but wanted to offer a DIY perspective!

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Ava Johnson

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Do you file electronically or mail in a paper form? I've heard mixed things about which is better.

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I file electronically through the DOL's EFAST2 system. It seemed more complicated at first, but now that I'm registered, it's actually easier than paper filing. The system catches basic errors before submission, which gives me more confidence that I'm doing it correctly. Electronic filing is also faster with confirmation that they received it. With paper forms, you never really know if they got processed correctly until much later. Just make sure to keep PDF copies of everything you submit for your records!

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Miguel Diaz

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Your CPA is being honest about their limitations. My previous accountant tried to help with my Form 5500 despite limited experience and completely messed it up. Cost me $5,200 in penalties that took months to get abated!!! Consider calling Schwab directly - since they're your plan provider, they might have resources or recommended partners who specialize in these filings. Many providers have relationships with TPAs who can handle this for reasonable fees.

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Zainab Ahmed

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Schwab told me they don't provide that service when I called last year. They gave me a list of third-party administrators but the cheapest was $375 for a basic filing. Is that normal pricing?

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$375 is actually pretty reasonable for Form 5500 filing services. I've seen TPAs charge anywhere from $300-800 for basic solo 401k filings, depending on the complexity and their service level. When you consider the potential penalties for mistakes (up to $250/day as mentioned earlier), that fee is like insurance against costly errors. Plus, they handle all the EFAST2 electronic filing requirements and usually provide compliance guidance for the following year. Shop around though - some charge less for straightforward situations.

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Freya Larsen

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I'm currently going through this exact same situation! Filed my return in early April and got hit with the ID verification requirement about 3 weeks later. Like you, absolutely nothing changed from previous years - same employer, same deductions, everything identical. It's incredibly frustrating to be randomly selected when you've done everything correctly. I completed the online verification through ID.me immediately after getting the letter, and I'm now at about 4 weeks post-verification with no updates. The "Where's My Refund" tool is completely useless - it just keeps saying "processing" with no timeline. I've been checking my transcript weekly and finally saw a 570 code appear, which from reading the comments here seems to indicate they're working on it. The waiting is absolutely brutal, especially when you're counting on that money for bills and expenses. It's wild how inconsistent the processing times are - some people get their refunds in 2 weeks while others wait 3+ months. Really hoping we both hear something soon because this whole process has been way more stressful than it should be!

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I'm in the exact same boat! Filed in mid-April, got the verification letter in early May, completed it right away, and now I'm at week 6 with zero updates. It's so frustrating how random and inconsistent this whole process is. The 570 code on your transcript is definitely progress though - I just saw that appear on mine too this week! From what everyone's saying here, that means they're actually working on our cases now. I've been trying to stay patient but it's hard when you're depending on that money. At least we know we're not alone in this nightmare process. Hopefully the 571 code shows up soon for both of us!

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I'm going through this exact same nightmare right now! Filed in early April, got flagged for ID verification in May (literally nothing changed from last year - same job, same everything), and I'm now at 8 weeks post-verification with still no refund. The inconsistency is absolutely maddening - I've seen people get their money in 10 days while others wait months for the exact same process. I finally broke down and used one of those services mentioned here to actually get through to an IRS agent, and they told me my verification was complete but there was some kind of secondary review happening that they couldn't give me a timeline for. The "Where's My Refund" tool has been stuck on "processing" this entire time, completely useless. I've been checking my transcript religiously and have seen the 570 code for weeks now but no 571 yet. Really hoping something breaks loose soon because I desperately need this money for some major expenses that I've been putting off. This whole system feels designed to frustrate people into giving up on their refunds.

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I'm so sorry you're dealing with this too! 8 weeks is absolutely ridiculous, especially when they completed your verification already. That secondary review thing sounds like what happened to several other people in this thread - it's like they're finding new ways to delay refunds even after you jump through their verification hoops. Have you tried any of those services people mentioned like Claimyr to get through to someone who might be able to push it along? At this point it sounds like talking to a human agent might be your only option to get some real answers. The 570 code sitting there for weeks without a 571 following it is so frustrating. Hopefully that secondary review wraps up soon and you finally see some movement!

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This is such a common issue with Airbnb hosts! I went through the same confusion last year. Here's what I learned after consulting with my CPA: You definitely need to report the full gross amount from your 1099-K on your Schedule C - this is what the IRS will be expecting to see since they receive a copy of that form from Airbnb. The key is then deducting all those Airbnb fees as legitimate business expenses. Look for these line items on Schedule C: - Line 10 for commissions and fees (this covers Airbnb's service fees) - Line 27a for other expenses (you can itemize things like payment processing fees) Also don't forget about other deductible expenses like cleaning supplies, repairs, utilities for the rental space, and depreciation on furniture/appliances used exclusively for the rental. I found it helpful to download all my transaction history from Airbnb for the year and create a simple spreadsheet tracking gross bookings vs. net deposits. This gives you a clear paper trail in case of any IRS questions later. The bottom line is your net rental income should end up being the same whether you report gross and deduct fees, or just report net - but matching the 1099-K is important for avoiding any red flags.

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This thread has been incredibly helpful! I'm in my second year of Airbnb hosting and just received my first 1099-K this year since my earnings crossed the $600 threshold. One thing I'm still confused about - if I use the standard mileage deduction for trips to my rental property for maintenance, cleaning, or guest issues, do I need to keep a detailed log of each trip? And can I deduct mileage for trips to buy supplies like toilet paper, towels, or cleaning products specifically for the rental? Also, for those who mentioned getting annual summaries from Airbnb - is there a specific place in the host dashboard where this is located? I've been digging around but can't seem to find anything that gives me a clean year-end breakdown that matches the 1099-K format. Thanks to everyone who shared their experiences with the various tools and services - definitely going to look into some of these options to make next year's filing easier!

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Miguel Silva

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Yes, you definitely need to keep a detailed mileage log for rental property trips! The IRS requires you to track the date, destination, business purpose, and miles for each trip. You can absolutely deduct mileage for supply runs - just make sure to note "purchased supplies for rental property" or similar in your log. For the Airbnb annual summary, try going to Host Dashboard > Insights > Earnings, then look for an "Export" or "Download" option that lets you select custom date ranges. Some hosts have found it under "Transaction History" with filters set to show the full year. If that doesn't work, the earlier suggestion about using Claimyr to reach Airbnb tax support might be your best bet - they can email you the proper breakdown. A simple smartphone app or even a notebook in your car works great for tracking mileage. Just get in the habit of logging it right when you start and end each trip!

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