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Ask the community...

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Sean Kelly

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My sister is a CPA and handled this exact situation for a client last year. The key was having detailed medical documentation that specifically stated: 1. The excess skin resulted from medically necessary weight loss surgery 2. The removal was necessary to prevent ongoing infections and discomfort 3. The procedure was not primarily for appearance reasons They had to document actual medical issues caused by the excess skin. She said without those documented medical reasons, the IRS rejected similar claims from other clients. One client even got audited over it.

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Zara Mirza

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Does the IRS ever pre-approve these kinds of deductions? I'm worried about claiming it then getting hit with penalties later.

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Sean Kelly

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The IRS doesn't offer pre-approvals for specific deductions before you file. They review after the fact if questions arise. The best protection is thorough documentation. This means doctor's letters clearly stating medical necessity, history of treatments for issues caused by the excess skin, and a clear connection between the gastric bypass and the need for skin removal. The better your documentation, the stronger your position if questioned later.

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Luca Russo

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Just want to add that I actually DID deduct my panniculectomy (medical tummy tuck) after losing 90lbs. I had a letter from my doctor documenting the recurrent infections and limited mobility. Make sure your surgeon codes it properly as medically necessary and not cosmetic! My procedure was coded as "panniculectomy for medical symptoms" not "abdominoplasty" which is considered cosmetic.

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That's really helpful! Did you have any issues with the IRS questioning the deduction? And did you need to get specific CPT codes included in your documentation?

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Don't stress about it! I was in a similar situation last year - college student, dependent on parents' taxes, and had some small crypto trades. Here's what I learned from my tax professor: 1) Capital losses (like your $6) can only help you on taxes, never hurt you 2) As a dependent, you only need to file if your income is above certain thresholds 3) Even if PayPal reports the transaction to the IRS (which they might not for such a small amount), it doesn't automatically mean you have to file The main thing is to keep records of the purchase and sale just in case, but this tiny transaction shouldn't impact your FAFSA or create any tax headaches.

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Would it be worth filing anyway just to establish the capital loss? I hear you can carry those forward to future tax years when you might have actual income.

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That's actually a good question about carrying forward the loss. Technically, yes, you could file just to document the $6 capital loss and carry it forward to future tax years. The IRS allows you to carry forward capital losses indefinitely until they're used up. However, for such a small amount ($6), it's probably not worth the effort of filing just for that. The time spent preparing and filing a return would far outweigh any potential future tax benefit from such a small loss. If the loss were larger (say, hundreds or thousands of dollars), then it would make more sense to file and establish that carryforward.

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Caden Turner

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Quick question - what happens if PayPal does send a 1099 for the crypto transaction? Will the IRS come after you if you don't file?

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The threshold for PayPal to issue a 1099-K for crypto in 2025 is $600 in total proceeds, so they probably won't send one for a single $500 transaction. But even if they did, the IRS matching system would see it was sold at a LOSS, not a gain. They generally don't pursue non-filers when there's no tax due (especially for dependent students). Just keep your records showing it was a loss transaction.

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Has anyone tried using just Excel or Google Sheets instead of paying for software? I'm super tight on cash while starting up and wondering if spreadsheets would work for the first year...

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Nia Harris

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I used Google Sheets for my first year in business and it was fine, but I only had about 10-15 transactions per month. I created columns for date, vendor, amount, category, and notes. Then had another sheet that totaled each category for tax purposes. Worked okay, but got tedious to maintain as I grew.

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Also, don't forget about saving for quarterly estimated taxes! This was my biggest shock when starting my business. The IRS wants you to pay taxes quarterly, not just at the end of the year. If you wait, you might get hit with penalties. I set aside about 30% of all income in a separate savings account for taxes. Better to have too much saved than not enough!

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Something else to consider with Section 179 that no one mentioned yet - you need to make sure your business actually has enough income to use the deduction in the first place. If your business shows a loss before the Section 179 deduction, you can't use it to further increase your loss. Also, remember that your state might treat Section 179 differently than the federal government! My state requires that I add back some of the federal Section 179 deduction and then deduct a smaller amount each year. Caught me by surprise my first time using it.

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Chris King

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If the business doesn't have enough income, can you carry forward the unused Section 179 amounts to future years? Or do you lose that deduction completely?

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Great question! You don't lose the deduction - any disallowed Section 179 deduction can be carried forward indefinitely until you can use it. So if your business doesn't have enough income this year, you can deduct it in future years when your income is higher. As for state treatment, it varies widely. In my state (California), they have a much lower Section 179 limit than federal and require the rest to be depreciated normally. Always check your specific state rules or talk to a local tax professional.

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Rachel Clark

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Another thing to consider - Section 179 is great for tax savings now, but remember that regular depreciation gives you the same total deduction over time. If you expect to be in a higher tax bracket in future years, it might actually be better to use regular depreciation to push some deductions into those higher-bracket years! I made this mistake with my consulting business a few years ago. Used Section 179 for everything when my income was relatively low, then when my income doubled two years later, I wished I had saved some of those deductions for when they would have saved me more in taxes.

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This is great advice! How do you decide which assets to use Section 179 on vs regular depreciation? Is there a rule of thumb?

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Rachel Clark

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I don't have a strict rule of thumb, but here's how I approach it now: For smaller purchases (under $10,000), I'll usually take Section 179 for the immediate benefit. For larger purchases, I look at my income projections for the next few years. If I expect my income to increase significantly or if I'm currently in a lower tax bracket than I expect to be in future years, I'll use regular depreciation. This spreads the tax benefit out to years when each dollar of deduction will save me more in taxes. It's also worth considering your cash flow needs. If you need tax savings now to reinvest in your business, Section 179 might make sense even if it's not mathematically optimal long-term. Tax planning is as much about your business strategy as it is about the technical details!

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One thing I didn't see mentioned yet - don't forget about state taxes if you're maintaining residency in a state with income tax. Even if you're traveling, if you keep your driver's license, voter registration, etc. in a state with income tax, you might still have filing requirements there. When I took a year off to travel, I officially changed my residency to a no-income-tax state (Florida) before leaving. Had to get a new driver's license, register to vote there, etc. It was a bit of a hassle but saved me from having to file state taxes in my high-tax previous state.

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That's a great point I hadn't considered! So if I keep my current state as my official residence while traveling, I'd still potentially need to file state taxes even if I'm not physically there or earning income there? Do you know if there's a minimum income threshold for state taxes similar to federal?

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Yes, exactly - if you maintain your legal residency in a state with income tax, you generally need to file there regardless of where you physically are during the year. It's based on legal domicile, not physical presence. State filing thresholds vary widely. Some states require you to file if you're required to file federal taxes, regardless of the amount. Others have their own thresholds that may be lower than federal ones. For example, California requires filing for single people who earned as little as $20,000 in 2024. I'd definitely check your specific state's requirements. When I was planning my year off, I found that calling the state tax department directly was the most reliable way to get accurate information for my situation.

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Omar Zaki

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Veteran here who did something similar a few years ago. Don't forget about your VA benefits while traveling! If you're planning to be overseas, make sure you understand how your VA healthcare works internationally (hint: it can be complicated). Also, if you're receiving disability compensation, that continues while traveling and is still tax-free, but you should set up direct deposit if you haven't already and use a bank that doesn't charge foreign transaction fees.

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Chloe Taylor

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I heard you need to report to the VA if you're out of the country for more than 30 days though? Something about benefits verification. Is that true?

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