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Fidel Carson

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Just to add on to what others have said, don't forget that with Schedule C you'll also need to pay self-employment tax (which is basically the FICA taxes that would normally be split between you and an employer). It's roughly 15.3% on top of your regular income tax. But the good news is you can deduct half of that self-employment tax on your 1040. Also, since you weren't having taxes withheld, you might get hit with an underpayment penalty unless you made estimated quarterly tax payments throughout the year. Just something to be aware of for next year if you continue freelancing!

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Oh no, I didn't make any quarterly payments! This is my first time dealing with self-employment. Will the penalty be really bad? And should I start making quarterly payments for this year right away?

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Fidel Carson

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The penalty usually isn't too severe - it's basically an interest charge on what you should have paid earlier. There are some safe harbor rules that might help you avoid it, especially if this is your first year with self-employment income or if your W-2 withholding from any other jobs covers at least 90% of your total tax liability. Yes, for 2025 you should plan on making quarterly estimated payments. The due dates are April 15, June 15, September 15, and January 15 (of the following year). You can use Form 1040-ES to calculate and submit these payments. It's much easier to pay a little each quarter than to be hit with a large bill at tax time!

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Has anyone used the HR Block online software for filing Schedule C? I'm in a similar boat (1099-MISC for some tutoring work) and wondering if their interface is good for first-timers with self-employment income? Or should I splurge for the paid version of TurboTax?

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Xan Dae

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I used HR Block last year for my Schedule C (freelance writing) and it was ok but not great. The interface was a bit confusing for business expenses. This year I switched to TurboTax Self-Employed and found it more intuitive - it asked better questions to help identify deductions I might have missed. It's more expensive but worth it if you have various expenses to deduct.

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My accountant told me that this is actually pretty straightforward. It IS income in the year you receive it, despite your intentions. What you do with the money afterward (saving it, spending it, giving it back) doesn't change the fact that it's income when received. But if you're planning to give it back as a gift later, just make sure you stay under the annual gift tax exclusion amount (currently $17,000) when you do give it to her, and you won't have any additional tax implications on that end.

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Does it matter if they're tracking it separately in a dedicated account? I've heard that can sometimes make a difference with the IRS if the money is clearly segregated.

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Keeping the money in a separate account is good practice and helps demonstrate your intent, but unfortunately it doesn't change the fundamental tax treatment. The IRS generally looks at the nature of the transaction when it occurs, not what you intend to do with the proceeds later. Having a separate account does provide a clear paper trail though, which is always helpful if questions ever arise. It shows you weren't trying to hide anything and had a specific purpose for the funds.

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Eli Butler

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Has anyone considered setting up a 529 college savings plan with this money instead? If your daughter might use it for education in the future, you'd still need to report the rental income BUT the money could grow tax-free if used for education expenses later. Might be a win-win?

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This is actually brilliant! My sister did something similar with her kids' "chore money" - she reported it properly as rental income but then put it in 529s for them. The growth being tax-free for education expenses made it really worthwhile.

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Just wanted to add - if you're using TurboTax, make sure you get the right version. The basic/free version doesn't support Schedule C. You'll need Self-Employed or possibly Home & Business. FreeTaxUSA handles Schedule C in their Deluxe version which is WAY cheaper than TurboTax tho. Also, make sure you're tracking all your business miles if you drive to different job sites for your renovation work! That adds up to a big deduction.

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NebulaNomad

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Is there a good app you recommend for tracking business miles? I always forget to log them and probably lost out on hundreds in deductions last year.

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I use MileIQ and it's been super helpful. It automatically tracks when you're driving and then you just swipe right for business trips and left for personal. Takes like 2 seconds per trip. Stride is another good one that's free, but I find it misses some trips since you have to manually start tracking. Either way, the standard mileage deduction is 65.5 cents per mile for 2023, so it adds up crazy fast especially for renovation work where you're going to different job sites!

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Anyone else notice their tax software always suggests amending previous years' returns? I used H&R Block last year for my cleaning business and it kept suggesting I amend 2022 to claim missed deductions. Is this just a way to charge more fees or actually worth looking into?

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Emma Taylor

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In my experience it's worth checking! I amended my 2022 return after ignoring that message for months and got an additional $1200 refund. I had missed some legit business expenses my first year. Different software sometimes finds different deductions.

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11 Just a heads up for anyone reading this thread - make VERY sure you're handling this correctly because 1099 reporting has gotten much stricter. If you're issuing 1099s, the amounts you report need to match what you put on your Schedule C. If there's a mismatch, it can trigger an automatic review.

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3 What's the threshold for needing to issue a 1099 to a contractor now? I thought it was $600 but someone told me it changed recently?

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11 The threshold is still $600 for payments made in the course of your trade or business. So if you paid a contractor $600 or more during the tax year, you need to issue them a 1099-NEC. This hasn't changed despite some rumors floating around.

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16 Stupid question maybe but do I need to include the payment processor fees when determining if I've hit the $600 threshold for issuing a 1099? Like if I paid someone $590 but with fees it was $608 total cost to me, do I need to issue a 1099?

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8 Not a stupid question at all! You would use the amount paid to the contractor ($590 in your example), not including the fees. Since $590 is below the $600 threshold, you wouldn't need to issue a 1099-NEC in this case.

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NightOwl42

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One thing nobody's mentioned yet - your coworker needs to be careful about state residency too, not just federal. New York is particularly aggressive about claiming tax residency. Since they were in NY for 6 months, NY will almost certainly consider them a statutory resident and try to tax their worldwide income. I learned this the hard way after working in Singapore for 7 months but maintaining my NY apartment. Even though I qualified for the Foreign Earned Income Exclusion federally, NY state still wanted taxes on my Singapore income!

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Oh wow, I hadn't even thought about the state tax implications. Do you know if there's any way around this? Would it help if they established residency in another state before going to Pakistan next time?

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NightOwl42

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Yes, establishing residency in a no-income-tax state before leaving for an international assignment can help. States like Florida, Texas, Nevada, etc. would be options. They would need to genuinely establish residency though - driver's license, voter registration, bank accounts, etc. For the current situation, they should look closely at NY's 183-day rule. If they were physically present in NY for fewer than 183 days and don't maintain a permanent abode there, they might have an argument against NY residency. However, with 6 months (approximately 180-183 days), they're right on the edge. Documentation of exact days in and out of NY will be critical.

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Has anyone mentioned Form 8833? For treaty positions like this, you might need to disclose the specific tax treaty provisions you're relying on using this form. I got hit with a penalty last year because I claimed a treaty benefit but didn't file the proper disclosure form.

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I've used Form 8833 before and it's actually not that bad. Just make sure your friend documents which specific article of the US-Pakistan tax treaty they're relying on. The form is pretty straightforward - just explains what treaty benefit you're claiming and why you qualify.

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