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Ask the community...

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Something nobody's mentioned yet - if you've been holding for over a year, you qualify for long-term capital gains rates which are MUCH lower than short-term. Depending on your income bracket, you might pay as little as 0% or 15% instead of your normal income tax rate. Also, if you sell at a loss, you can deduct up to $3,000 against ordinary income per year and carry forward any additional losses to future tax years. Don't let the 8949 form complexity keep you from making sound financial decisions! Just use good software to track everything.

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Thanks for pointing this out! Actually a lot of my holdings would qualify for long-term capital gains rates since I've held most for 2+ years. I didn't realize the rate could be as low as 0-15% depending on income bracket. Is there a specific income threshold for each rate?

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For 2025 tax year, long-term capital gains rates work like this: 0% rate applies if your taxable income is under $47,025 for single filers or $94,050 for married filing jointly. The 15% rate applies if your income is above that but below $518,900 for single or $583,750 for married filing jointly. Above those upper thresholds, it's 20%. These rates are much better than short-term gains, which are taxed as ordinary income and can go up to 37% depending on your tax bracket. Definitely worth considering when deciding when to sell!

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NeonNomad

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Just want to warn people that even if wallet-to-wallet transfers aren't taxable, you NEED to keep immaculate records of them. If you get audited and can't prove which transfers were between your own wallets, the IRS might treat them all as sales. I learned this the hard way. Document everything, keep screenshots of transfers, save your wallet addresses, and use a good tracking system. Better to have too much documentation than not enough.

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How do you recommend documenting wallet ownership? I have like 5 different wallets across different platforms and hardware devices.

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Rita Jacobs

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One thing nobody mentioned yet - keep track of ALL your expenses related to your freelance work! As a self-employed person, you can deduct: - Portion of your phone bill used for business - Any design software subscriptions - Computer equipment (partially) - Home office space (if you have a dedicated area) - Marketing expenses - Website costs I learned this the hard way my first year freelancing and missed out on tons of deductions. Start a simple spreadsheet now to track everything!

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Harold Oh

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What about stuff I already bought last year? Can I still claim those expenses even if I don't have all the receipts anymore?

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Rita Jacobs

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You can absolutely claim expenses from last year even without receipts, though having some documentation is always better. Bank or credit card statements showing the purchases can work as backup. The IRS doesn't require receipts for expenses under $75 (though it's still good practice to keep them). For bigger purchases like a computer or equipment, definitely try to find some proof of purchase. Remember you can only deduct the percentage used for business - so if your laptop is 60% for freelance work and 40% personal, you'd deduct 60% of the cost. Start keeping better records now for this year!

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Khalid Howes

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quick question - if your parents are still providing more than half your support (like paying for housing, food, etc) can they still claim you as a dependent even if you file your own taxes? my situation is similar to OP's.

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Amun-Ra Azra

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Yes! This is a common misunderstanding. You can file your own tax return AND still be claimed as a dependent on your parents' return if you meet the criteria (which includes them providing more than half your support). The key thing is that if you're claimed as a dependent, you can't claim your own personal exemption. But you still need to file your own return if you meet the income thresholds, which it sounds like you do.

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Lena Schultz

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One thing nobody's mentioned - the "reasonable compensation" requirement for S corps doesn't necessarily mean you have to pay yourself regularly throughout the year. The IRS cares about the annual amount being reasonable for your role and industry, not the frequency. I've been running annual payroll for my S corp for 3 years now. I use Gusto, which charges a base fee of $39/month plus $6/person. So yes, I pay the monthly fee year-round, but the simplicity is worth it to me. In December, I run payroll once I know what my business profits will be, making sure my salary meets that "reasonable compensation" threshold. For Form 941, I file every quarter marking zeros for the first three quarters. It's annoying but takes like 10 minutes once you know how to do it. Some states also require quarterly unemployment tax filings even with zero wages. The real headache isn't the payroll itself but documenting why your salary is "reasonable" - keep good records of industry salary surveys, time spent working, etc.

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Have you ever tried asking the payroll service to waive the fees for the months you're not running payroll? I've heard some people have had success with that, especially if you tell them you're considering switching to a pay-as-you-go provider.

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Lena Schultz

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I actually did try negotiating with Gusto my first year, but they wouldn't budge on the monthly base fee. They explained that even when I'm not running payroll, their system is still maintaining my account, handling compliance updates, and keeping my data secure. I looked into pay-as-you-go options, but for my situation, the convenience of staying with one system and having all my historical data in one place was worth the extra cost. Plus, Gusto handles all my tax filings automatically, which saves me time with those quarterly Form 941s. I just check the numbers before submission.

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Pedro Sawyer

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I just want to point out that there's a third option beyond "subscribe and cancel payroll service" or "pay monthly fees all year" - you can use a CPA that offers payroll services. My accountant charges me a single fee for year-end S corp payroll processing rather than monthly fees. They handle everything - calculating the optimal salary based on my business profits, preparing the W-2, filing Form 941 for that quarter, and ensuring I've met the reasonable compensation requirements. They also keep records to justify my compensation in case of audit. For the other three quarters, they file the Form 941 with zeros as needed. The total annual cost is significantly less than paying a monthly subscription to a payroll service, and I don't have to think about it until December.

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Mae Bennett

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Do you have any ballpark on what your CPA charges for this service? I'm trying to compare options and everything seems so expensive for basically running payroll once a year.

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Pedro Sawyer

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I pay about $350 for the annual payroll processing, which includes all the year-end forms, tax filings, and payroll calculations. They also charge about $75 per quarter for filing the zero-wage Form 941s, so all in I'm paying around $575 annually. This was much cheaper than the $468+ I would pay for the annual subscription to even the most basic payroll services ($39/month). Plus, I get the benefit of having professional eyes on my numbers who can advise on optimal salary levels and help document reasonable compensation determinations.

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Something similar happened to me in 2023! If it helps ease your mind, I can tell you my experience. I mailed my return late (in May) without an extension, but I was due a refund like you. No penalties at all. Got my refund after about 10 weeks. The IRS is really only concerned with punishing people who owe them money and pay late. Since you're owed a refund, you're basically just letting them hold onto your money longer, which they're happy to do. Just make sure you keep copies of EVERYTHING you sent them, including that explanation letter. And if you're really worried, you might want to check your tax transcript on the IRS website after a month or so to see if there's any activity.

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Yuki Sato

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That's a huge relief to hear about your experience! Did you ever get any kind of notice or update from them before the refund showed up? I'm wondering if I'll be completely in the dark until money suddenly appears in my account.

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I didn't get any notices beforehand at all. The money just showed up in my account one day. The only way I knew they were processing it was by checking the "Where's My Refund" tool on the IRS website, which finally updated after about 8 weeks to show they had received my return. After that, it took about 2 more weeks for the refund to arrive. So yeah, you'll probably be in the dark for a while. Paper returns really do disappear into a black hole for a couple months. If you need the money urgently, that's when I'd recommend trying to talk to someone at the IRS directly.

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Just a tip for next year - always save your AGI (Adjusted Gross Income) from the previous year's tax return. That's often why e-filing gets rejected with "already filed" errors - the system uses your prior year AGI to verify your identity. If you enter it wrong, it can trigger that error message even though no one has actually filed your return.

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Dylan Wright

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This happened to me too! Turns out I had rounded my previous year's AGI instead of using the exact number. Such a stupid reason for rejection.

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One thing no one has mentioned yet - there's a difference between not taking deductions and incorrectly reporting your income. You don't have to take every deduction you're eligible for, but you DO have to accurately report all your income. So if you're thinking about not reporting legitimate business expenses to keep your income higher for EITC purposes, that gets into a gray area. For self-employed people, business expenses directly reduce your Schedule C income, which affects both your AGI and EITC. I'd be very careful about intentionally skipping deductions that directly affect how income is reported vs. those that are purely optional after your income is already correctly stated.

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Jacob Lewis

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Can you give an example of what would be considered optional vs. required reporting? I'm in a similar situation with my dad who has some 1099 income along with disability.

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Business expenses on Schedule C would be part of correctly reporting your net business income - skipping those could be seen as misrepresenting your income. These directly affect your AGI and therefore your EITC. Things like choosing the standard deduction instead of itemizing medical expenses would be completely optional and wouldn't affect your EITC either way, since both happen after your AGI is calculated. Similarly, you can choose whether to claim certain tax credits you're eligible for - that's your choice and won't affect other calculations.

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Something to consider: the EITC has different income thresholds based on filing status and number of qualifying children. For 2025, with one qualifying child, EITC begins to phase out around $46,500 for single/head of household. If your sister's income is right at one of these thresholds, small changes in AGI can have a big impact on the credit amount. This might explain why you're seeing significant changes in the EITC calculation when making adjustments. Most tax software will let you try different scenarios to see what gives the best outcome. Just make sure whatever you submit is truthful - the difference between optimizing your return and misrepresenting information is a critical line you don't want to cross.

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Ethan Clark

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This is a really important point. My accountant explained that the EITC has these "cliff edges" where just a few hundred dollars difference in income can change your credit by a thousand dollars or more. Worth running the numbers carefully if you're near one of these thresholds.

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