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Ask the community...

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Nora Bennett

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Something to consider is whether you can treat this property as a partial business use during the elder care period. If you can document that the property was being used specifically for elder care purposes, you might be able to claim certain expenses as deductible medical expenses. The IRS allows deductions for medical care facilities in some cases. While your situation doesn't fit neatly into the tax code categories, a creative tax professional might be able to help you structure this in a favorable way.

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Ryan Andre

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That's a really interesting angle! I did something similar when my father moved in with us. We were able to deduct a portion of our utilities and even some modifications to the house as medical expenses. But I think you need documentation from a doctor recommending the living arrangement for medical purposes.

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Lauren Zeb

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Has anyone mentioned Section 121(c) partial exclusion? If the primary reason for the sale was your grandmother's death (which counts as an unforeseen circumstance), you might qualify for a partial exclusion of gain based on how long you used it as a primary residence during the 5-year period ending on the date of sale. The formula would be: (shorter of: time used as primary residence during 5-year period OR time between event and sale) Γ· 2 years Γ— $250,000 exclusion So even if you don't get the full exclusion, you might get a partial one that could save you significant taxes!

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This is really helpful information, thank you! If I understand correctly, I would calculate how long I used it as a primary residence within the 5 years before selling, divide that by 2 years, and multiply by $250,000? In my case, I hadn't lived there personally for about 6 years before selling, so would that mean I get zero exclusion under this calculation?

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Lauren Zeb

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Since you hadn't lived in the home as your primary residence during the 5-year period before the sale, you're right that the first part of the calculation would be zero. However, there's still potentially the second part - the time between the qualifying event (your uncle's death) and the sale. If the sale was primarily due to your uncle's passing, and you sold within a reasonable time after that event (which sounds like you did since it took about a year to sell), you might still qualify for some level of partial exclusion based on that timing. I'd strongly recommend consulting with a tax professional who can review all the specific dates and circumstances, as the calculations can get quite complex and the IRS rules have some nuances that might work in your favor.

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Alfredo Lugo

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Pro tip: If you're choosing between H&R Block and TurboTax mainly for the Rakuten deal, check both services before deciding. Sometimes TurboTax offers better cash back percentages than H&R Block. Right now H&R Block is higher at 16%, but that can change throughout tax season. I've seen TurboTax go up to 20% cash back at times.

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Emma Morales

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Thanks for this! Do you know how often the cash back percentages change? Should I wait until closer to the filing deadline to see if the rates go up?

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Alfredo Lugo

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The cash back percentages typically change every 2-4 weeks, sometimes more frequently during peak tax season. They usually increase as we get closer to April 15th, but there's no guarantee. Last year the highest rates were actually in mid-March, then they dropped slightly in April. If you don't need to file immediately, checking back every week or so might help you catch a better rate. Just don't cut it too close to the deadline in case of technical issues.

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Sydney Torres

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Don't forget you can also use coupons WITH the Rakuten cash back! I found a code for 25% off H&R Block Premium which stacked with the 16% Rakuten cash back. Just Google "H&R Block coupon codes 2025" and try a few until you find one that works.

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This worked for me! Found a coupon for 20% off and it stacked with the Rakuten cash back. Ended up paying like $79 for Premium instead of $119, then got about $12 back through Rakuten. Every bit helps when you're paying taxes!

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Andre Laurent

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Something everyone's missing here - if you're gambling that much, the casino might have already reported your winnings to the IRS on a W-2G if you hit certain thresholds (like $1,200+ on a slot machine win). If that's the case and you don't file, you're gonna get a nasty letter from the IRS later because they'll know you had that income! Also, make sure your parents know about your gambling income. If it's too high, they might not be able to claim you as a dependent anyway which could mess up their taxes too.

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Luca Conti

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Thanks for mentioning this! I haven't received any W-2G forms yet, but I did have a couple of bigger wins that might have triggered reporting. Would the casino have given those to me right away when I won, or would they mail them later? Also, do you know what the income limits are for my parents to claim me as a dependent? I'm a full-time student.

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Andre Laurent

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Casinos typically mail W-2Gs by January 31st for the previous year's winnings, though for larger wins they often complete the paperwork at the time of payout. If you had wins over $1,200 on slots or $5,000 on poker/table games, you should expect to receive them. For your parents to claim you as a dependent while you're a full-time student under 24, there's no income limit, but you must not provide more than half of your own support. The support test looks at who pays for your housing, food, education, etc. - not just your income. So even with your gambling winnings, if your parents still provide more than half of your total support, they can claim you. But if those winnings meant you provided more than half of your own support this year, that could change your dependent status.

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Quick tip from someone who used to work at a casino: keep EVERYTHING for documentation. The IRS loves to audit gambling winnings. Save your player's club statements, ATM receipts from the casino, even parking receipts to prove you were there. Create a log of your gambling sessions with dates and amounts won/lost. If you took cash to gamble with, document when you withdrew it. The more records you have, the better position you'll be in if questioned about your winnings vs losses.

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Is this really necessary for a college student with only $8,500 in winnings? Seems like overkill. The IRS isn't going after small fish like this when there are millionaires to audit.

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Former tax preparer here. For amounts this small, it's really not worth amending. The IRS computer systems have tolerance thresholds built in, and a $4 difference won't trigger any action. If you really want to be 100% by the book, you can file a paper amendment for free, but honestly, the postage stamp would cost almost as much as the tax owed. Most practitioners I know wouldn't bother with an amendment for anything under $50 in tax difference.

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Omar Hassan

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If they do have these threshold amounts, why doesn't the IRS just publish them? Seems like it would save everyone a lot of time and stress over tiny amounts.

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They don't publish the exact thresholds for a strategic reason. If everyone knew precisely what amount they could "get away with" not reporting, many people would deliberately stay just under that threshold, and the cumulative effect across millions of taxpayers would be significant. The IRS wants everyone to report everything accurately, but they have to allocate their limited enforcement resources effectively. They keep these internal tolerance levels confidential and also change them periodically to prevent systematic abuse.

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Quick question - if I'm in a similar situation but I OVERPAID by a small amount ($10-20) because I missed a deduction, is it worth amending to get that money back? Or is the same "too small to bother" rule apply?

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Diego Vargas

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For overpayments, the calculation is different. You're getting YOUR money back, so it depends on how much your time is worth. A refund of $20 might be worth the 30-45 minutes it takes to prepare and mail a paper amendment. Remember though, paper amendments can take 6-12 months to process currently, so you'll be waiting a while for that $20.

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RaΓΊl Mora

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One thing nobody's mentioned yet - you need to start keeping your business and personal expenses SEPARATE! Get a dedicated credit card for all your freelance expenses. Trust me, trying to sort through a year's worth of mixed expenses at tax time is a nightmare. Also, look into SEP IRA or Solo 401(k) options. Even with a smaller side income, you can make retirement contributions as both the employee AND employer which gives you a nice tax deduction now and builds retirement savings. It's basically the one silver lining of paying self-employment taxes.

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Margot Quinn

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Is there a minimum amount you need to make from self-employment to open a Solo 401k? I'm just starting out with freelance work too.

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Evelyn Kim

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Make sure you track EVERYTHING for your Schedule C! As someone who's been freelancing for years, here's what you can typically deduct: - Software (like Adobe - you can allocate a % for business use) - Hardware (laptop, etc. - with depreciation) - Internet (% used for business) - Phone (% used for business) - Office supplies - Professional development (courses related to your design work) - Business insurance if you have it - Portion of rent/mortgage for home office (if you have a dedicated space) - Utilities for that same % of your home Just make sure everything you deduct is ORDINARY and NECESSARY for your business. That's the IRS standard. And keep receipts for EVERYTHING!

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