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Ask the community...

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Yara Nassar

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Have you tried asking the cleaning company how they're reporting this payment to you? That might give you a clue about how they expect you to file it. Usually companies don't issue 1099-NECs unless they consider you an independent contractor rather than an employee.

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I did call them but the office manager wasn't sure. They just said their accountant told them to issue 1099s for all referral partners who got over $600. They don't care how I file it on my end, just that they reported the payment to the IRS.

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Yara Nassar

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That makes sense - the $600 threshold is the standard for when businesses must issue 1099s. Based on that and what others have said here, it sounds like Schedule C is definitely your answer. The cleaning company is treating you as an independent contractor for these referrals (separate from your regular HVAC employment). Remember that with Schedule C income, you're responsible for both the employer and employee portions of Social Security and Medicare taxes, which comes out to about 15.3%. That's calculated on Schedule SE. You'll want to make sure you're setting aside enough to cover this additional tax burden.

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StarGazer101

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Don't forget you get to deduct 1/2 of your self-employment tax on your 1040! A lot of people miss this deduction. And if you use a portion of your home exclusively for managing these referrals, you might qualify for a home office deduction too.

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The home office deduction is super strict though. You need a space used EXCLUSIVELY for business. If you use your dining table for paperwork but also eat there, it doesn't qualify.

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StarGazer101

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You're absolutely right about the exclusive use requirement. The space must be used regularly and exclusively for business purposes to qualify for the home office deduction. A dedicated desk or room that's only used for managing these referrals would qualify, but a multi-purpose space like a dining table wouldn't. It's also worth mentioning that there are two methods for calculating the home office deduction: the regular method (based on actual expenses and the percentage of your home used for business) and the simplified option (a standard deduction based on the square footage of your office space). For someone with a small amount of self-employment income like the OP, the simplified method might be easier.

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Anita George

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One thing no one mentioned yet - if you sold your old house in 2023, but were still paying the mortgage in 2022, you should absolutely deduct that interest on your 2022 taxes! It doesn't matter if you lived there for 11 months or 2 months in 2022, what matters is: 1) You owned the property 2) It was a qualified residence (your primary home or second home) 3) You paid mortgage interest in 2022 The 1098 forms will show exactly how much interest you paid in 2022 regardless of when you sold the house. Just be aware of the $750k combined limit as others mentioned. You'll need to do some calculations if your total mortgage debt exceeds that amount.

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Does this still apply if the old house was vacant for the last month of 2022? We moved out completely but it didn't sell until 2023, so it was just sitting empty for December 2022.

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Anita George

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Yes, it absolutely still applies even if the house was vacant. The mortgage interest deduction is based on ownership of a qualified residence, not occupancy. As long as you owned the home and it was either your primary residence or second home for some portion of the year, you can deduct the interest you paid. The IRS actually allows for temporary absences (even if you're not physically living there) as long as the home is not rented out during that period. So your vacant house in December still qualifies for the mortgage interest deduction on your 2022 taxes.

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Logan Chiang

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Has anyone used H&R Block software for handling two properties? I'm having trouble figuring out where to enter both 1098 forms and how to deal with the $750k limit. The software keeps acting like I can only enter one property!

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Isla Fischer

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I used TurboTax last year for a similar situation and it had a specific section where you could enter multiple mortgage interest statements. Look for something like "I have more than one mortgage" or "Add another 1098 form" option. It should be somewhere after you enter the first 1098. For the $750k limit, the software should automatically calculate this if you enter all your mortgage information correctly, including the date each mortgage originated and the original loan amounts.

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Logan Chiang

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Thanks for the suggestion! I looked again and found a tiny "Add another property" button I completely missed before. Now I see where to enter both properties. Still confused about the $750k limit though - I guess I'll just trust the software to calculate it correctly.

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Former tax preparer here. Another big reason for discrepancies: state tax calculations. The federal math is usually more straightforward, but state taxes can vary widely in how they're calculated by different software. Some states have weird quirks that certain software handles better than others. Also check if you're comparing apples to apples. Make sure all the software is calculating both federal AND state, or just federal. That can make a huge difference too!

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Which software do you think is most accurate overall from your experience? I've been using TaxAct but I'm wondering if I should switch.

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There isn't really one "most accurate" across the board. It depends on your specific tax situation. TurboTax tends to be very thorough for complex situations involving self-employment or investments. TaxAct is solid for more straightforward tax situations and much more affordable. H&R Block has better support if you might need help. FreeTaxUSA is great value for slightly complex returns.

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Melissa Lin

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UGHHH I did my taxes THREE times this year with different services and got refunds ranging from $1,235 to $1,842!!! How is this even legal?? I ended up going line by line through the generated forms and found that the difference was mainly in how they handled my 1099 side gig income and home office deduction. TurboTax found deductions the others missed but FreeTaxUSA had a lower prep fee.

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The fees can make a huge difference in what you actually get back. Sometimes the software that finds you the biggest refund also charges the highest preparation fee, which can totally cancel out the benefit!

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Chris Elmeda

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7 Something important to note that I don't think anyone mentioned yet - you'll want to make sure you have Form 8606 filled out correctly for both tax years. This form is crucial for documenting non-deductible IRA contributions and conversions. For your 2022 recharacterization, you might need to file an amended return for 2022 if you've already filed, depending on how you initially reported the contribution. For the 2023 conversion, you'll report it on your 2023 Form 8606. TurboTax should walk you through this, but sometimes it misses the nuances of recharacterizations across tax years. Double-check that both years' Form 8606 shows the correct basis and converted amounts.

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Chris Elmeda

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15 Wait, so I might need to amend my 2022 return? I already filed it last year and reported the contribution to my Traditional IRA, but the conversion didn't happen until 2023. Do I really need to go back and change something from last year's filing?

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Chris Elmeda

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7 No, you likely don't need to amend your 2022 return. If you correctly reported the 2022 Traditional IRA contribution on your 2022 return (on Form 8606 showing it as non-deductible), then you're fine for that year. The conversion that occurred in 2023 (even of 2022 contributions) gets reported on your 2023 return. The key is making sure your 2022 Form 8606 established your basis correctly, and then your 2023 Form 8606 shows the conversion. TurboTax should handle this if you input everything correctly in the IRA/retirement sections.

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Chris Elmeda

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11 Has anyone had success using the "backdoor Roth IRA" tool in TurboTax? I found this specific feature last year that walks you through exactly this scenario - contributions and conversions that span tax years. It's not super obvious to find but it made my similar situation much easier to report correctly.

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Chris Elmeda

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22 I tried using that feature but got confused when it asked about recharacterizations vs conversions. It seemed to treat them as completely different things, but in my mind they're related. Did you find it actually worked correctly for your situation?

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Micah Trail

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This sounds like your doctor friend is trying to avoid paying his share of employment taxes by making you a 1099 contractor instead of a W-2 employee. Classic move by small business owners trying to save money. Here's what you need to consider: 1. If he controls when and where you work, provides equipment, and directs how you perform tasks, you're legally an EMPLOYEE, not a contractor. 2. The "business" he wants you to create would just be a pass-through entity that doesn't change these facts. 3. The IRS has specific tests for worker classification and misclassification can lead to penalties. Don't let him off-load his tax obligations onto you! If you're functioning as an employee, you should be classified as one.

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Nia Watson

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But aren't there legitimate advantages to being a contractor? I've heard you can deduct all kinds of things as business expenses - home office, car, phone, even meals sometimes. Couldn't those deductions make up for the extra taxes?

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Micah Trail

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There are some legitimate advantages to being a contractor, but they rarely outweigh the costs for most workers. Yes, you can deduct business expenses, but there are strict rules about what qualifies. Home office deductions require exclusive use of that space for business. Vehicle deductions only apply to business use, not personal or commuting. Meal deductions are limited to 50% and must be directly related to business. These deductions rarely offset the additional 7.65% self-employment tax burden, loss of unemployment benefits, lack of workers' comp protection, no paid time off, and no employer-provided health insurance. Plus, you take on all the administrative burden of tax filings, estimated quarterly payments, and keeping meticulous records. For most personal assistants, employee status is financially advantageous unless the contractor rate is significantly higher.

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I'd be worried about the 1099 vs W-2 classification issue here. If you're working regular hours, getting direct supervision, and only working for this one doctor, the IRS might see this as employee misclassification regardless of what you call it. Read up on Schedule C and self-employment taxes before you agree to anything! And definitely look at the IRS's 20-factor test for worker classification - just Google it.

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The 20-factor test is actually outdated. The IRS now uses a simplified approach with three categories: Behavioral Control, Financial Control, and Relationship of the Parties. Much easier to understand than the old system. https://www.irs.gov/businesses/small-businesses-self-employed/independent-contractor-self-employed-or-employee

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