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Ask the community...

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Drake

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Has your CPA discussed the potential benefits of a tax-free reorganization under Section 368? Depending on your specific situation, there might be ways to restructure the company that could facilitate the ownership transition with more favorable tax treatment.

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Sarah Jones

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Section 368 reorganizations typically involve C corporations, not S corps. They're really designed for more complex corporate structures. For a family S corp, it would likely be overkill and might even jeopardize their S election.

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Honorah King

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One strategy that hasn't been mentioned yet is considering a self-canceling installment note (SCIN). This could be particularly valuable given your mom's desire to step back from the business and your 5-7 year timeline. With a SCIN, your mom would sell her shares to you and your sister in exchange for installment payments, but the note automatically cancels if she passes away before it's fully paid. This provides several benefits: it removes the remaining unpaid balance from her estate for tax purposes, gives her income during her lifetime, and allows you to potentially acquire the shares at a discount to reflect the cancellation risk. The payments would need to be higher than a regular installment sale to account for this risk, but it could provide significant estate tax savings if structured properly. This approach works particularly well when the selling family member is older or has health concerns. You'd definitely want your attorney and CPA to model this carefully, as the IRS has specific valuation requirements, but it's worth exploring alongside the other options mentioned here.

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Ethan Clark

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This is a really interesting option I hadn't heard of before! The SCIN approach sounds like it could work well for our situation since mom is in her early 70s and the timeline fits. A few questions: How do you typically determine the appropriate "premium" for the cancellation risk? And would this type of arrangement affect the S Corp's ability to make distributions to shareholders during the payment period? I'm wondering if there are any restrictions on cash flow that might impact our ability to make the required payments. Also, are there any specific valuation requirements from the IRS that make this more complex than a standard installment sale?

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Ethan Brown

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its not worth it tbh. just wait for ur actual refund. the fees eat up so much of the advance its basically a payday loan w extra steps šŸ’…

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@Ethan Brown totally agree! I made that mistake a couple years ago. The fees were like $40-60 just to get my own money a week early. Better to just be patient and keep the full refund amount šŸ’Æ

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Pro tip from someone who's been through this multiple times - the TurboTax advance offer typically shows up right after you complete all your forms but before you hit the final submit button. You'll see your estimated refund amount first, then they'll show the advance option if you qualify. But honestly, after reading all these comments about the fees, I'd suggest just filing early and waiting for the actual refund. The IRS is processing returns pretty quickly this year anyway!

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Paolo Ricci

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This is super helpful! @Issac Nightingale do you know roughly how long the IRS is taking to process returns this year? I m'new to filing and trying to figure out if it s'worth waiting vs getting the advance. The fees everyone s'mentioning sound pretty steep 😬

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Luca Ferrari

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Don't forget that even after you estimate your federal payment, each state handles extensions differently! I learned this the hard way. For example, California automatically gives you the extension if you get a federal one, but you still need to pay the estimated amount. New York requires its own extension form AND payment. Some states don't charge interest if your estimate is reasonable while others are strict about it. Make sure you check your specific state's rules about extensions and payments - don't assume they follow the federal guidelines.

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Thanks for bringing this up! Do you know if there's a quick resource that breaks down different state requirements? My situation is even more complicated because I moved mid-year and had income in multiple states.

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Luca Ferrari

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There isn't really one perfect resource that covers all states, but the Federation of Tax Administrators (taxadmin.org) has links to all state tax agencies where you can find the specific rules. For multi-state situations, each state you earned income in will have its own requirements. Most tax software platforms also have state-specific guidance built in if you're using one. They'll usually walk you through the proper forms needed for each state. With income in multiple states, you definitely want to be careful since some states have reciprocity agreements while others don't.

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Nia Wilson

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Just to add something here that nobody mentioned - make sure you remember to pay ESTIMATED TAXES too if you're self-employed or have other income without withholding! This is separate from your extension payment. Q1 estimated taxes for 2025 are also due April 15th, the same day as the 2024 tax year deadline. So you might need to make TWO payments - one for what you still owe for 2024 (your extension payment) and one for Q1 estimated taxes for 2025. I made this mistake and got hit with penalties even though I thought I'd done everything right with my extension.

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Omg this is so important! I completely forgot about this last year and got hit with both penalties AND interest. It's especially confusing because you're paying for two different tax years on the same day. Do you just make two separate payments to the IRS and indicate which is which somehow?

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Yes, you make separate payments and specify what each one is for! When you pay online through EFTPS or the IRS website, there are different payment type codes. For your 2024 extension payment, you'd select "Form 1040 Extension" or "Balance Due" and specify tax year 2024. For Q1 2025 estimated taxes, you'd select "Estimated Tax" and specify tax year 2025. If you're mailing checks, you write separate checks and include the appropriate vouchers - Form 4868 for the extension payment and Form 1040ES for the estimated payment. Make sure to clearly mark the tax year on each payment to avoid any confusion with IRS processing. This dual payment situation catches so many people off guard! It's definitely worth setting a reminder for yourself since missing either one can result in penalties.

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Free and Low-Cost Tax Filing Options for 2025 Filing Season

Alright tax people, I've been researching free and budget-friendly tax filing options for this upcoming tax season and wanted to share what I found! There seem to be lots of choices for filing individual returns (Form 1040 series) depending on your situation. I've broken it down into three main categories: self-filing options, self-filing with assistance, and completely free tax preparation programs. I'll try to highlight special options for military members, those needing to file prior years, Form 1040-NR filers, US expats, and people with stock transactions too. **Self-Filing Options** *Available from late January through October 17 for current tax year* If your 2024 Adjusted Gross Income (AGI) is under $79,000, I definitely recommend starting with IRS Free File. My Free Taxes from United Way also connects you with a free version of TaxSlayer if your AGI is under that $79k threshold. Important tip: You MUST click through the links on these official websites to get truly free filing! Both IRS Free File and the My Free Taxes version of TaxSlayer should handle any type of income without extra charges as long as you're under the AGI limit. This means no surprise fees for self-employment, 1099 forms, gig income, unemployment, etc. Don't make the mistake of going directly to a company's website - they'll usually try to upsell you. TurboTax and H&R Block aren't part of the IRS Free File Alliance anymore, so I generally don't recommend them for truly free filing. Has anyone else found other reliable free/low-cost options I missed?

Has anyone tried FreeTaxUSA? I've used it for the past 2 years and it's been really good. Federal filing is completely free regardless of income or complexity (I have investments, HSA, and 1099 income), and state is only like $15. The interface isn't as fancy as TurboTax but it gets the job done without upselling you constantly.

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I second FreeTaxUSA! Used it last year after TurboTax tried to charge me $89 for having an HSA. FreeTaxUSA handled everything perfectly - even my crypto transactions and home office deduction. Their customer service was surprisingly good too when I had a question about my state return.

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Nolan Carter

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This is such a comprehensive breakdown - thank you for putting this together! I've been dreading tax season but this makes it seem much more manageable. Quick question about the AGI threshold for IRS Free File - is that $79,000 based on your 2024 income or your 2023 income from last year's return? I'm right around that number and want to make sure I'm looking at the right year's income to determine eligibility. Also, for anyone who's used multiple free options, how do they compare in terms of user-friendliness? I'm not super tech-savvy and get overwhelmed by complicated interfaces. Would love to hear which ones are most straightforward to navigate!

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Just to add to what others have said - as a sole proprietor LLC, your business doesn't file its own tax return. Instead, you report the income and expenses on Schedule C of your personal tax return (Form 1040). And yes, the threshold is $400 net profit, not $5,000.

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What's the difference between gross income and net profit for this $400 threshold? Like if I made $2,000 in sales but spent $1,700 on supplies and expenses, would I still need to file?

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The $400 threshold refers to net profit, which is your gross income minus your business expenses. In your example, if you made $2,000 in sales but had $1,700 in legitimate business expenses, your net profit would be $300. Since that's below the $400 threshold, you technically wouldn't be required to file based solely on your self-employment income. However, keep in mind there might be other reasons you'd need to file a tax return, and it's generally a good practice to file anyway so you have documentation of your business activity, especially if you plan to claim business losses.

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Diez Ellis

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One thing nobody mentioned - even if you're under the $400 threshold, you might still want to file taxes for your business. Filing can establish your business history (helpful for loans later) and let you claim startup losses to offset future profits. My accountant had me file even when I only made $275 my first year.

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This is super helpful. I've been on the fence about filing since I only made about $300 with my new photography business. Do you think it's worth paying for tax software or a professional just to file when I made so little?

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