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Just to add something important - if your in-laws were primarily living on Social Security and VA benefits, there's a good chance they weren't required to file at all. Many people don't realize this. For example, in 2022, a married couple over 65 only needed to file if their gross income exceeded $28,700. Social Security is often not counted in this calculation unless they had other substantial income. VA benefits are generally tax-free. Before you panic about years of unfiled returns, find out if they were even required to file. This could be much simpler than you think!
Thank you for mentioning this! I had no idea there were income thresholds where filing wasn't required. That makes me feel a bit better about the situation. Their mobile home was probably worth about $25,000 and they had no other major assets. Do you know if the IRS can tell us whether they were required to file for those years?
Yes, the IRS can absolutely help determine if they were required to file. When you contact them (either directly or through a service like others mentioned), ask specifically for "wage and income transcripts" for the years in question. These will show all income reported to the IRS under their Social Security numbers. The value of their mobile home actually doesn't factor into the filing requirement - it's based on income, not assets. Given what you've described, it sounds very possible they weren't required to file. The 1041-ES forms you received are likely related to the estate itself, not their personal unfiled returns, which is a separate matter that the IRS can clarify when you speak with them.
One thing nobody's mentioned - you should check if the estate itself needs to file a return. Form 1041-ES is for estimated tax payments for estates and trusts. If the estate generated income after your in-laws passed (like interest on accounts, sale of assets, etc.), the estate might need to file its own return separate from your in-laws' personal returns. Usually this only applies if the estate earned more than $600 in income before assets were distributed to heirs. Did the estate have any income-generating assets that weren't immediately distributed?
This is important! My mom's estate had a CD that generated $700 in interest during probate, and we had to file a 1041 for the estate even though she wasn't required to file personal returns for years before her death.
Thank you for bringing this up! There was a small checking account with maybe $3,000 that earned some interest, and a life insurance policy that paid out about $15,000. Would the life insurance payout count as estate income? We distributed everything pretty quickly after getting the insurance money, probably within 2-3 months.
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Something that hasn't been mentioned yet - if you're staking through a DeFi protocol rather than a centralized exchange, the record-keeping gets WAY more complicated. I had to figure this out for my Curve and Aave staking. For DeFi staking, you'll need to track: 1. Initial deposit 2. Each reward distribution (and USD value at that moment) 3. Any compounding/restaking 4. Final withdrawal Make sure you're noting which blockchain everything happened on too, especially if you're staking across multiple chains.
Omar Fawzi
ā¢Do you have any tips for tracking DeFi staking rewards if you were, hypothetically, completely disorganized and didn't track anything all year? Asking for a friend... š¬
If your "friend" hasn't been tracking anything, there are a few options! First, check if the DeFi protocols you're using have any dashboard that shows historical rewards - some newer ones do offer this. For most cases though, you'll need to use a blockchain explorer like Etherscan, Solscan, etc. Look up your wallet address and filter for the contract addresses of the staking protocols you used. You'll need to go through the transactions and identify the rewards. It's tedious but possible. Some tax tools can also retroactively analyze your on-chain activity and categorize staking rewards automatically. Worth the investment if you have significant DeFi activity, especially across multiple chains or protocols.
Chloe Wilson
One more thing I didn't see mentioned - staking rewards may also be subject to self-employment tax if you're considered to be in the "trade or business" of crypto staking. This typically happens if your staking operation is substantial, involves significant time/effort, and you're actively managing it as a business activity. For most casual stakers with a few validators, ordinary income treatment (without SE tax) is appropriate. But if you're running a serious node operation and staking is your primary income source, you might need to consider SE taxes too.
How much staking would trigger that self-employment consideration? I'm running 3 Ethereum validators and about 10k in Polkadot. Is that enough to be considered a "business"?
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Aisha Khan
5 Don't forget about self-employment tax! Since this is independent contractor work, you'll owe an additional 15.3% on top of your regular income tax for Social Security and Medicare. At six figures, this is going to be a significant amount. I'd recommend putting aside at least 30-35% of your income for taxes going forward. Also, you should definitely start making quarterly estimated tax payments this year to avoid underpayment penalties. The due dates are April 15, June 15, September 15, and January 15 of the following year.
Aisha Khan
ā¢15 Is there any way to reduce that self-employment tax? That's a huge chunk of money on top of regular taxes!
Aisha Khan
ā¢5 You can reduce your self-employment tax by forming an S-Corporation instead of operating as a sole proprietor. With an S-Corp, you pay yourself a reasonable salary (which is still subject to self-employment tax) but can take the rest of your profits as distributions that aren't subject to SE tax. However, there are additional costs and complexities with an S-Corp, including payroll processing, separate tax returns, and other compliance requirements. Generally, it's not worth considering until you're consistently making at least $80-100K in profit. Given your income level, it might be worth consulting with a tax professional who specializes in small businesses to see if this strategy would benefit you.
Aisha Khan
19 Does anyone know what happens if I just don't report some of this income? Like I got a 1099 from one platform but most of my income is just direct payments that aren't tracked that way.
Aisha Khan
ā¢8 BAD idea. The IRS has been cracking down hard on unreported income, especially from payment apps. As of 2022, platforms like CashApp, Venmo, PayPal etc. are required to report transactions to the IRS if they total over $600 in a year. Even if you don't get a form, they're sending the info to the IRS. Plus, if you have large deposits going into your bank account that don't match your reported income, that's a major audit flag. The penalties for intentional underreporting can include up to 75% of the unpaid tax plus interest, and potentially criminal charges for tax evasion. Not worth the risk with six-figure income!
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Don't forget that even if your vacation rental qualifies as non-passive, you still need to watch out for the At-Risk Rules and Excess Business Loss limitations. These can limit how much of your losses you can deduct in a given year regardless of the passive/non-passive classification. I learned this the hard way last year when I thought I could deduct my entire $45k short-term rental loss, only to find out the Excess Business Loss rules limited my deduction to a much smaller amount. Just something to keep in mind as you work through this.
Natalie Chen
ā¢Thanks for mentioning this! What exactly are the Excess Business Loss limits for 2025? I've been so focused on the passive vs non-passive issue that I totally overlooked this potential limitation.
For 2025, the Excess Business Loss limitation is $300,000 for single filers and $600,000 for joint filers. This means if your total business losses exceed your business income by more than these thresholds, the excess gets carried forward to future years. For most people with a single vacation rental property, this limit isn't an issue. But if you have multiple properties or other business losses, it could come into play. The At-Risk Rules are potentially more relevant in your case - they limit your deductible losses to the amount you have "at risk" in the activity, which typically includes your cash investment, the portion of loans you're personally liable for, and certain qualified non-recourse financing.
Am i the only one who thinks its absurd that something this important isn't clearly spelled out in Pub 527?? Like why do we have to piece together info from random regulations and forums to figure this stuff out?
Ruby Garcia
ā¢Totally agree! I feel like half of tax law is hidden in obscure regulations that normal people would never find. It seems like they make it intentionally complicated.
Eloise Kendrick
OP, I think your situation definitely calls for a professional, but don't go back to H&R Block. They're overpriced for what they offer. Find an actual CPA who specializes in individual taxes. The stock sales alone make this worthwhile - especially if they were RSUs or options from your employer, which have special tax treatment. When I was in a similar situation (moved states, had stock sales), I missed some deductions doing it myself that cost me thousands. The next year I used a CPA who found errors in my previous return and helped me file an amendment that got most of that money back. The $500 I paid was totally worth it.
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KaiEsmeralda
ā¢Thanks for this perspective! I definitely won't go back to H&R Block after that experience. Do you have any tips on finding a good CPA who knows how to handle these interstate moves and stock issues? Is there anything specific I should look for or ask when I'm interviewing them?
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Eloise Kendrick
ā¢Look for a CPA who specializes in individual taxes rather than business taxes. Ask specifically about their experience with interstate moves and stock compensation (RSUs, options, etc). A good question is "how would you handle allocation of income between California and Oregon for a mid-year move?" Also ask about their approach to organizing those old 401ks - a good tax professional thinks beyond just this year's return. Check Google reviews, but also ask for referrals from colleagues in similar situations. Since you work for a large company, there might be others who've dealt with the same stock and relocation issues who can recommend someone.
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Lucas Schmidt
Anyone have recommendations for tax software if OP decides not to use a CPA? I had a somewhat similar situation (moved states, sold stock) but used FreeTaxUSA instead of TurboTax and saved a bunch of money while still getting all the forms I needed.
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Freya Collins
ā¢I'll second FreeTaxUSA. It handled my interstate move and stock sales for $15 (for the state return). Federal filing is completely free regardless of complexity. TurboTax would have charged me $120+ for the same forms.
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Lucas Schmidt
ā¢Thanks for confirming! I felt like I was taking a risk trying a less-known software but it worked perfectly. The interface isn't as pretty as TurboTax but it asks all the right questions and handles the complex scenarios at a fraction of the cost.
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