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Has anyone actually tested this liability protection in real life? I have a similar structure but my attorney warned me that courts can sometimes "pierce the veil" if the businesses aren't truly operated as separate entities.
I work in commercial insurance and this is a really important point. The liability protection only works if you maintain proper separation between the entities. This means: - Separate bank accounts for each LLC - Proper contracts between the entities if they do business with each other - Separate books and records - Properly signed documents using the correct entity names - Adequate capitalization for each entity - Following all corporate formalities If you don't do these things, a court might indeed "pierce the corporate veil" and allow creditors to reach assets in other entities.
This thread has been incredibly helpful in clarifying the S-Corp owning LLCs structure. I'm in a similar situation with multiple business ventures and was also confused about the terminology. One thing I'd add based on my research is that you'll want to consider the state-level implications too. While federally the LLCs owned by your S-Corp will be treated as divisions, some states have different rules for state tax purposes. For example, some states require separate LLC tax filings even when they're federally disregarded entities owned by an S-Corp. Also, regarding the liability protection discussion - make sure you understand that while the LLC structure protects between business lines, it doesn't protect you personally from professional liability in businesses where you're directly involved. If you're providing professional services through any of these LLCs, you'll still have personal exposure for your own actions, regardless of the entity structure. The holding company approach with an S-Corp owning multiple LLCs is definitely a solid strategy for what you're trying to accomplish, just make sure your implementation covers all the operational details mentioned in the comments above.
Great point about state-level considerations! I'm just getting started with understanding business structures and hadn't even thought about the fact that federal and state tax treatment could be different. When you mention some states requiring separate LLC filings even when they're federally disregarded - does that mean you'd potentially have to file tax returns in multiple states if your LLCs operate in different states? That could get complicated quickly. Also, the professional liability point is really important. I was thinking the LLC structure would protect me from everything, but you're right that if I'm personally providing services, I'd still have personal exposure for my own mistakes regardless of the entity structure. Sounds like professional liability insurance would still be necessary even with this setup. Thanks for adding those practical considerations - it's exactly the kind of real-world details that help someone new to this understand what they're actually getting into!
Has anyone dealt with the "14 day rule" along with the family rental situation? I'm planning to use my rental property occasionally throughout the year (less than 14 days) while also renting to my nephew. Not sure if this complicates the 80% FMV requirement.
The 14-day rule still applies, but it makes documentation even more important. If you use the property yourself for 14 days or less (or 10% of the days it's rented, whichever is greater), you can still treat it as a rental property assuming you're charging at least 80% FMV to your nephew. Just make sure you keep extremely detailed records of exactly which days you personally used the property. The IRS scrutinizes family rentals with personal use much more carefully. Document everything!
Something else to keep in mind is that the IRS also looks at the terms of your rental agreement when determining if it's a legitimate rental. Even if you're charging 80% of FMV, if your lease agreement with your family member is too informal or doesn't include standard rental terms (like security deposits, maintenance responsibilities, eviction clauses), the IRS might still question whether it's truly a rental arrangement. I'd recommend drafting a formal lease agreement that you'd use with any tenant - specify the monthly rent, security deposit requirements, who's responsible for utilities and maintenance, lease duration, and termination conditions. Treat it like a business transaction even though it's family. This documentation will support your position that it's a legitimate rental if you're ever audited. Also, make sure you're actually enforcing the lease terms. If you let your family member skip payments or don't follow through on lease provisions, that could undermine your argument that it's a true rental property.
This is excellent advice about the formal lease agreement! I hadn't thought about how the informality of the arrangement could work against me. You're absolutely right that even at 80% FMV, the IRS could still question the legitimacy if it doesn't look like a real rental business. I'm curious - what happens if a family member does miss a payment or two? Obviously we'd want to avoid that, but life happens. Is there a certain threshold where occasional missed payments wouldn't jeopardize the rental classification, or does any leniency automatically make it look like personal use? Also, do you know if the security deposit needs to be at market rate too, or just the monthly rent? I was thinking of asking for a smaller deposit since it's family, but now I'm wondering if that's a mistake.
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.
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?
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.
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.
This is such a frustrating situation, and I really feel for you dealing with this bureaucratic nightmare. The fact that you were being responsible by keeping money with the IRS instead of taking refunds only to potentially owe later makes this even more maddening. I'm curious - when you say you've been doing this pattern for years of rolling over overpayments, do you have documentation of previous years where this worked without issue? If the IRS accepted and applied these credit elections in prior years without problems, that might help establish that their current interpretation is inconsistent with their own past practices. Also, have you requested a complete account transcript for all the relevant years? Sometimes there are processing entries or notes in the IRS system that aren't visible to frontline agents but could be crucial for an appeal. The transcript might show exactly how and when they handled your payments, which could reveal processing errors or inconsistencies. One more thought - if you can demonstrate that following the IRS's own guidance led to this situation (like if their forms or publications suggested that credit elections would preserve your funds), that might be grounds for arguing they should be estopped from enforcing the strict limitation period against you. Definitely agree with the attorney recommendation - $75K is absolutely worth professional help, especially since there may be procedural deadlines for appeals that you can't afford to miss.
Something people don't realize about the refund statute - if you file your amended return even ONE DAY after the 3-year window closes, the IRS is legally required to reject your refund claim. The tax code gives them zero flexibility on this. I work in a tax office and see people heartbroken when they miss the deadline by just a short time. The most painful one was a client who mailed their amendment on the last day but didn't use certified mail, so there was no proof of timely filing. The IRS received it 4 days later and denied a $7,800 refund. Don't take chances with these deadlines!
Is there any exception at all? What about if you were in the hospital or had some serious issue that prevented you from filing? Seems incredibly harsh that there's no appeals process.
Unfortunately, there are very limited exceptions to the refund statute deadline. The IRS does have some provisions for "equitable relief" in extreme circumstances like natural disasters, but these are incredibly rare and hard to qualify for. Things like hospitalization or personal emergencies typically don't qualify unless they meet very specific criteria. The statute is written into the tax code itself, so even IRS agents who want to help you can't override it. This is why it's so important to act quickly once you discover a potential refund - don't wait thinking you have plenty of time. I always tell people to treat the refund statute deadline like it's written in stone, because legally, it pretty much is.
I just went through this exact situation last year with my 2020 taxes! The stress is real when you realize there might be money on the table. Here's what I learned: First, don't panic - if you filed your 2020 return by the extended deadline (May 17, 2021), you actually have until May 17, 2024 to file an amended return. That means you likely still have time if you're just discovering this now. The key thing is to act fast once you know about it. I procrastinated for months thinking "I'll get to it eventually" and almost missed my deadline. File Form 1040-X as soon as you can gather all your documentation for those business expenses you missed. One tip - make sure you have really solid documentation for those business expenses. The IRS will scrutinize amended returns more carefully, especially for business deductions. Keep receipts, invoices, and any records that prove the expenses were legitimate and business-related. $3,200 is definitely worth pursuing! Don't let the IRS keep money that's rightfully yours just because of paperwork anxiety. You've got this!
Jackson Carter
Great question! I was in the exact same situation when I started my freelance consulting business. Here's the key difference that helped me understand: **Schedule C** is for your business - so all that income from selling your handmade crafts online goes here, along with any business expenses like materials, shipping costs, packaging supplies, etc. This directly affects your self-employment tax too. **Schedule A** is for personal itemized deductions - your medical expenses and charitable donations would go here, but only if the total of all your itemized deductions exceeds the standard deduction (which is pretty high these days). For your craft business, definitely keep detailed records of everything - receipts for supplies, mileage to craft fairs, even a portion of your internet bill if you use it for the business. These all reduce your taxable business income on Schedule C. One tip: consider setting up a separate bank account for your craft business if you haven't already. Makes tracking so much easier come tax time!
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Dmitri Volkov
ā¢This is super helpful! I'm just starting out with a small online business too and the separate bank account tip is gold. Quick question - if I use my personal car for business deliveries or picking up supplies, can I deduct those miles on Schedule C? And do I need to track every single trip or is there some kind of estimate I can use?
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Romeo Barrett
ā¢Yes, you can absolutely deduct business mileage on Schedule C! You'll need to track each business trip though - the IRS requires detailed records. I recommend keeping a simple log in your car or using a mileage tracking app on your phone. Record the date, destination, purpose, and miles for each trip. For 2024, the standard mileage rate is 67 cents per mile for business use, which is usually better than trying to deduct actual car expenses. Just make sure you're only counting miles that are specifically for business - like going to the post office to ship orders, picking up craft supplies, or driving to craft fairs. Your regular commute doesn't count. The separate bank account really does make everything so much cleaner come tax time. You'll thank yourself later when you're not trying to sort through months of mixed personal and business transactions!
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Mateo Hernandez
This is such a great question and one that trips up so many new business owners! I went through the exact same confusion when I started my consulting practice. The simplest way I explain it to people is: - **Schedule C** = Your BUSINESS money (income from crafts, business expenses like materials, shipping, etc.) - **Schedule A** = Your PERSONAL deductions (medical bills, charity donations, mortgage interest, etc.) For your craft business, you'll definitely need Schedule C to report that income and claim business deductions. Whether you need Schedule A depends on if your itemized personal deductions (medical expenses + charitable donations + other qualifying expenses) add up to more than the standard deduction for 2024, which is $14,600 for single filers. Pro tip: Keep those business and personal expenses completely separate from day one. I learned this the hard way when tax time came and I was scrambling through bank statements trying to figure out what was what! A separate business checking account or even just a dedicated credit card for business purchases makes life so much easier. The business deductions on Schedule C are especially valuable because they reduce both your regular income tax AND your self-employment tax. Every receipt for craft supplies, packaging materials, or business-related travel is money back in your pocket!
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Lilly Curtis
ā¢This breakdown is super clear, thanks! I'm just getting started with my side business and had no idea about the self-employment tax implications. Quick question - you mentioned keeping business and personal expenses separate, but what about things that are mixed use? Like if I use my home internet for both personal browsing and running my online craft store, or my phone for both personal calls and business communications with customers? Can I still deduct a portion of those on Schedule C?
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