I work at a tax prep place part time during tax season, and I can tell you we see this confusion with 1099-K forms all the time. For the 2024 tax year, the threshold is definitely $5,000 for reporting purposes. But here's the important thing - receiving a 1099-K doesn't automatically mean that money is taxable income. It's just an information reporting form. When clients come in with 1099-Ks from personal transfers, we document the nature of the transfers and exclude them from taxable income.

Based on what I've seen with similar situations, you're likely fine as long as you can document that these are personal transfers and not payments for goods or services. The key is keeping good records showing the money flow - that your roommate receives money from family, sends it to you, and you withdraw it for him. Since you mentioned around $6,800 total, you're above the $5,000 threshold where CashApp might issue a 1099-K. But even if you receive one, it doesn't mean you owe taxes on that money. You would just need to explain on your tax return that these were non-taxable personal transfers. I'd suggest keeping screenshots or records of the transfers showing they're from your roommate (not business transactions), and maybe even a simple written agreement between you two documenting this arrangement. That way if any questions come up, you have clear documentation that you're just facilitating access to his own money to help him avoid fees. The IRS understands that people use these apps for personal transfers, so as long as you can show the money wasn't actually income to you, you should be okay.

I've been through this exact scenario with multiple S-corps over the years. The practical reality is that basis-only corrections rarely trigger IRS scrutiny when there's no tax liability change. However, I'd strongly recommend creating a paper trail regardless of which route you choose. Here's what I typically advise clients: Issue the corrected K-1 marked "AMENDED" and create a detailed memo explaining the error, the correction, and confirming zero tax impact. Keep this with your corporate records. If you're really concerned about potential matching issues, you could file a superseding 1120-S if you're still within the original filing deadline (including extensions), which avoids the formal amendment process. The $800 your accountant wants seems excessive for what should be straightforward paperwork. As a sole shareholder, you have more flexibility here than multi-owner entities. Just make sure whatever you do is well-documented in case questions arise later.

As someone who's dealt with similar K-1 corrections, I'd recommend taking a middle-ground approach that balances compliance with practicality. Since you're the sole shareholder and there's no tax liability impact, you have more flexibility than most. Here's what I'd suggest: First, create a comprehensive correction memo documenting the original error, the corrected amounts, and explicitly stating there's no change to tax liability. Include calculations showing your correct stock basis before and after. Then issue yourself an amended K-1 clearly marked "AMENDED" and reference the memo. For the 1120-S question - if you're really concerned about potential IRS matching issues down the road, consider calling them directly to ask about your specific situation. Sometimes getting their guidance on record can provide peace of mind and documentation that you acted in good faith. The reality is that basis-tracking corrections rarely trigger enforcement action when there's no revenue impact, but having solid documentation is what protects you regardless. Your $800 accounting fee seems steep for what's essentially a paperwork correction with no tax consequences.

9 Just adding another suggestion: call your employer's payroll department directly (not your manager). I work in HR and we can generate duplicate W-2s instantly with our payroll system at no charge. It's ridiculous they're trying to charge you $75! If it's a larger company, go above your boss's head and contact corporate payroll. By law, employers must provide W-2s to employees, and most companies don't charge for replacements.

As a tax preparer, I want to emphasize that you have several legitimate free options before paying your employer anything. The IRS wage and income transcript is your best bet - it's official, free, and most financial aid offices accept it. You can get it instantly online at irs.gov if you can verify your identity, or request it by phone. Also, definitely try calling your employer's corporate HR or payroll department if it's a larger company. Many employers don't charge for duplicate W-2s, and your manager might not be following company policy. The $75 fee sounds excessive and potentially against company guidelines. If all else fails and you're still within the tax filing deadline, you can actually file your taxes without the W-2 using Form 4852 (Substitute for Form W-2) based on your final pay stub, but check with a tax professional first since you're a dependent.

Don't forget about state taxes! While the federal government generally doesn't tax foreign inheritances, some states do have inheritance taxes. What state do you live in? That could make a difference too.

I went through something similar when my grandmother in France passed away and left me some money. One thing I learned that might help you - make sure you keep detailed records of EVERYTHING from the moment you're notified about the inheritance. I'd recommend creating a file with: the original will (and English translation), all correspondence with the Italian lawyer, bank transfer documents showing the source of funds, any Italian tax documents, and records of the exchange rate on the day you receive the money. The IRS loves documentation, and having this paper trail ready will save you headaches if they ever have questions. Also, don't rush to transfer the money immediately. Take time to understand all the requirements first - both the Form 3520 reporting and any potential FBAR obligations if the money sits in Italy for a while. I made the mistake of moving too quickly and had to reconstruct some of the documentation later. The €120,000 is a significant amount, so even though you won't owe income tax on it, getting professional help for at least the first year's filing is probably worth the cost to make sure everything is done correctly.

7 One thing nobody's mentioned yet - remember you can choose SPECIFIC LOTS when selling RSUs. You don't have to sell entire batches. Many brokers default to FIFO (first in, first out) but you can typically select exactly which shares to sell. This lets you fine-tune your tax strategy even further.

5 Just adding another consideration - if you've got other income/loss events this year, that might influence your decision. I ended up selling some underwater RSUs (at a loss) to offset gains from other investments. Tax-loss harvesting can be a powerful strategy!