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Besides watching those income thresholds, don't forget about Roth conversions as a potential strategy. If your mom has traditional IRAs or 401ks, you might want to strategically convert some to Roth during lower-income years. While this creates taxable income in the year of conversion, it reduces future Required Minimum Distributions that could push her over the Social Security taxation thresholds in coming years. This is especially valuable if she's not yet 73 (when RMDs must start) as you have a window of opportunity before those mandatory withdrawals kick in.

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Jade Lopez

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I hadn't thought about Roth conversions at all. How would you determine how much to convert each year? Is there some kind of sweet spot?

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You want to convert just enough each year to "fill up" her lower tax brackets without pushing her into a bracket where the tax cost becomes too high. It's often best to convert amounts that keep her in the 10% or 12% federal brackets. For the Social Security taxation specifically, you'd ideally convert amounts that keep her combined income (AGI + nontaxable interest + 1/2 of SS benefits) below $25,000 if possible, or at least below $34,000 to avoid the 85% taxation threshold. Many people find converting $5,000-8,000 per year strikes a good balance, but it's very specific to her overall financial situation.

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Nina Chan

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Has anyone used any specific tax software that handles this Social Security Tax Torpedo situation well? I've used TurboTax for years but it doesn't seem to provide much guidance on how to avoid SS taxation for next year.

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Ruby Knight

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I've had good luck with H&R Block Premium. It has a feature that lets you run scenarios for the following year and shows how different income levels affect your Social Security taxation. Not perfect but better than TurboTax for this specific issue in my experience.

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For what it's worth, I worked with QOFs last year as part of my job. If you had invested in one, you would 100% know about it. They're not something you accidentally invest in. The paperwork is substantial, and the fund manager makes it very clear what you're investing in because the tax benefits are their main selling point. Also, if you had a QOF investment, you would have received a special statement from them for tax purposes. So if you haven't received anything specifically mentioning "Qualified Opportunity Fund" or "Opportunity Zone," you can safely mark "No" on Schedule D.

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Ana Rusula

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Thank you so much for confirming this! It sounds like QOFs are very specific investments that I would definitely remember if I had bought into one. That makes me feel a lot better about checking "No" on my Schedule D. Do you think there's any reason the IRS might flag my return if I indicate I don't have QOF investments?

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There's virtually no reason your return would be flagged for marking "No" on the QOF question if you don't have QOF investments. The IRS already knows who has these investments because the funds themselves must file Form 8996 to self-certify as QOFs, and they report their investors. These investments are relatively uncommon compared to standard retirement and brokerage accounts. The question is on Schedule D mainly to ensure people with actual QOF investments properly report them. For the vast majority of taxpayers, "No" is the correct answer and won't raise any red flags.

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Just to add to what others are saying - Qualified Opportunity Funds are still relatively niche investments. I've been investing for over 15 years and have never accidentally stumbled into one through normal investing channels. Most major brokerages like Vanguard, Fidelity, etc., might offer them, but they're marketed specifically for their tax advantages and typically require higher minimum investments.

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Do these QOFs actually perform well as investments? Or are people just using them for the tax benefits? Wondering if they're something worth looking into.

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Chloe Wilson

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Another thing nobody mentioned yet is that sometimes these ultra-wealthy people use their company perks to reduce personal expenses, which is another form of tax avoidance. Like when a company pays for "business travel" on a private jet, security personnel, housing for "business purposes," etc. These are business expenses for the company (tax deductible) but provide personal benefit to the executive without counting as taxable income. Musk for example has used company resources for personal security and travel - completely legal if structured properly, but effectively gives him benefits that would otherwise require taxable income.

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Is that why so many rich people set up random side businesses? My neighbor claims his boat as a business expense for his "fishing charter company" that mysteriously never has any customers lol

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Just to add another layer to this conversation - one thing the "buy, borrow, die" strategy relies on is the stepped-up basis rule at death. This means that when someone inherits assets, the cost basis resets to the market value at the time of inheritance. Example: If Musk bought Tesla stock at $10 and it's worth $1000 when he dies, normally selling would trigger capital gains tax on the $990 profit. But his heirs get a stepped-up basis to $1000, so if they sell at $1000, they pay ZERO capital gains tax on all that appreciation. This is why super wealthy people can borrow against assets their whole lives, never sell, and then pass enormous wealth to the next generation without anyone ever paying capital gains tax on decades of appreciation. It's completely legal but definitely a huge advantage that most average people can't access.

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I went through this exact situation with my LLC last year. One thing to watch out for - if you ever had ANY kind of tax election for your LLC (like S-Corp status), you might need to formally revoke that election when closing the EIN. My accountant didn't catch this, and I ended up getting a notice about "missing returns" a year after I thought everything was closed. Turns out I needed to file Form 8832 to change my entity classification back before closing. Might not apply to your situation since you were always a partnership, but something to be aware of!

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I don't think we ever made any special elections - we were always just a simple pass-through partnership. But that's a good thing to double-check. Is there a way to confirm what elections might be in effect for an EIN?

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You can verify any tax elections by calling the IRS Business & Specialty Tax Line at 800-829-4933. When you get through, request your "entity control information" and they can tell you exactly how your LLC is classified and any elections that are in effect. For most simple LLCs that never filed anything special, you're probably fine. But if you or your accountant ever filed forms like 2553 (S-Corp election) or 8832 (entity classification election), you'll want to address those specifically. In my case, I had elected S-Corp status years earlier and forgot all about it!

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Simple question - did you have a business bank account for this LLC? If so, make sure that's properly closed too before finalizing the EIN closure. I made the mistake of closing my EIN while my business checking account was still open, and it caused a real mess with the bank later on since they required an active EIN for business accounts.

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Amina Diop

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Good point! Also check if you had any business credit cards, vendor accounts, or state tax accounts (like sales tax permits) that need to be closed separately. Those don't automatically close when you dissolve the LLC or close the EIN.

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Have you checked to see if your employer incorrectly reported the stock exercise on their end? I had a similar issue where my company reported my RSUs on a 1099-B but I reported them as W-2 income (which was correct), and the IRS computer system flagged it as unreported income. Took nearly a year to sort out.

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Beth Ford

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Oh that's interesting! I hadn't considered that. I worked for a startup so it's totally possible they messed something up with the reporting. How did you end up resolving your situation? Did you have to get documentation from your employer?

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I had to get a corrected Form W-2 from my employer showing the stock compensation was included in my wages. Then I had to write a detailed letter to the IRS explaining exactly how the income was reported on my tax return (which line number, which form, etc.) and included copies of my brokerage statements showing the transactions. The key was getting someone from our HR/payroll department to provide a letter confirming how they had reported it to the IRS. Once I had that documentation and sent everything certified mail, it eventually got resolved. Just be prepared for it to take several months.

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Raul Neal

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You might want to request a tax advocate if this keeps dragging on. It's a free service from the IRS where they assign someone to help resolve complicated cases. Google "IRS Taxpayer Advocate Service" - they can often cut through red tape faster than you can on your own.

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Jenna Sloan

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Tax advocates are nearly impossible to get right now unless you're facing "significant hardship" like eviction or utilities being cut off. They're seriously understaffed and have strict criteria for who they'll help. I tried for months and kept getting rejected.

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