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One thing to consider: if you go the route of filing the SS-8 form and your employer finds out, be prepared for potential tension or even looking for a new job. I went through this exact situation as a home health aide last year. My employer was FURIOUS when they got the letter from the IRS about my classification status. Even though I was 100% right (and the IRS eventually ruled in my favor), my employer made things pretty uncomfortable until I eventually found a new position. Just something to keep in mind - being right doesn't always make the situation easier in the short term. Document EVERYTHING from this point forward in case you need it later.

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That's what I'm worried about. I really need this job and don't want to burn bridges, but I also don't want to pay extra taxes I shouldn't have to pay. Did you end up having to pay the full self-employment tax before the IRS determination came through?

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I actually used Form 8919 when I filed my taxes, which allowed me to only pay the employee portion of the Social Security and Medicare taxes while my SS-8 determination was pending. That way I didn't have to pay the full self-employment tax. If the IRS had eventually determined I was actually a contractor (which they didn't), I would have had to pay the difference later. But it allowed me to file on time without overpaying. My tax preparer was familiar with the situation and helped me with the proper coding on the form.

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Kylo Ren

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Has anyone tried just showing the employer the actual IRS website about household employees? My sister had this exact situation and literally just pulled up the IRS page on her phone during a conversation with her employer. The page specifically says nannies are household employees: "Household workers such as housekeepers, maids, babysitters, gardeners, and others who work in or around your private residence as your employee are subject to employment taxes." Her employer actually didn't realize they were breaking tax law and fixed the situation once they saw the official IRS guidance. Sometimes it's just ignorance rather than malice.

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I tried this approach with my employer last year and it worked! Sometimes people just don't know the rules. I printed out the relevant IRS publication and highlighted the parts about household employees. When I showed them, they were actually relieved to have clear guidance and issued me a correct W-2.

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For what it's worth, I've been a homeowner for 8 years now and there's another consideration with a December purchase - property tax payments. Check to see if you prepaid any property taxes at closing or if there was a proration of property taxes between you and the seller. Those can be deductible in the year paid (2020) even if your mortgage payments didn't start until 2021. Also, don't forget to check if you qualify for any first-time homebuyer credits or programs! Different states have different programs, and while the federal first-time homebuyer credit isn't available anymore, some states still offer incentives.

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Do you know if homeowner's insurance premiums are ever tax deductible? I think I prepaid 14 months at closing and wondering if any of that is deductible anywhere.

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Unfortunately, homeowner's insurance premiums aren't tax deductible for personal residences. They're considered a personal expense rather than a deductible housing expense. The only exception would be if you use part of your home for business - then you might be able to deduct the business portion of your insurance. However, if you paid for mortgage insurance premiums (different from homeowner's insurance), those might be deductible depending on your income level and when you got your mortgage. The rules change frequently on mortgage insurance deductibility, so that's worth looking into for your specific situation.

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Has anyone had experience with the timing of the mortgage interest statements? My lender told me that interest paid at closing in December should have been included on my 1098 for the following year. Is that normal? Seems like they should give me a 1098 for both years if I paid interest in both years.

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Jayden Reed

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In my experience, most lenders only issue a 1098 if the total interest for the year exceeds $600. If you closed in late December, the few days of interest probably didn't hit that threshold, so they might have just included it in next year's form. You can still deduct it in the correct year though, even without a separate 1098.

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I've been using TurboTax for years but switched to a CPA when my tax situation got more complicated with rental property and self-employment. Here's my take: Use TurboTax if: - You're comfortable with basic tax concepts - You have time to research deductions yourself - You're willing to double-check everything - You want to save money ($100-150 vs $300-500+) Use a CPA if: - You have multiple income sources or complicated deductions - You want personalized tax planning advice - You're afraid of an audit - You value peace of mind over saving money For your specific situation, I'd probably lean toward TurboTax or that taxr.ai tool someone mentioned, unless you hate dealing with taxes or have more complications you didn't mention.

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Rhett Bowman

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Would you say the same applies for H&R Block? I've always used them in-person because I'm paranoid about making mistakes, but it costs me around $350 each year for what seems like a pretty simple return.

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H&R Block's storefront preparers are generally not CPAs but trained tax preparers with varying experience levels. They're in a middle ground - more personalized than software but typically less knowledgeable than a dedicated CPA. For a straightforward return, you're probably overpaying at $350. Their software is on par with TurboTax but much cheaper, around $50-100 depending on the version. If you're comfortable trying software but want some backup, H&R Block does offer a hybrid option where you can start online but get help from a tax pro if needed. Bottom line: If your return is fairly simple, either tax software or the AI tool mentioned would likely be more cost-effective than continuing to pay $350 at H&R Block. But if that peace of mind is worth $250+ to you each year, there's value in that too!

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Don't forget you can get TurboTax totally free if your income is under $73k through the IRS Free File program! Even with $95k you might qualify for discounted versions through some partners. Check https://www.irs.gov/filing/free-file-do-your-federal-taxes-for-free first before paying full price anywhere.

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Daniel White

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This isn't entirely accurate. The $73k limit is for the IRS Free File program partners, but TurboTax actually left that program last year. They have their own "free" version but it's very limited in what forms it supports. With education expenses and retirement account transfers, OP would definitely get bumped to a paid tier.

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23 Don't forget about FBAR requirements if you're receiving a large sum from abroad! If you have more than $10,000 in foreign accounts at any point during the year (including temporarily during this transaction), you need to file an FBAR (FinCEN Form 114). This is separate from your tax return and has huge penalties if you miss it.

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1 But if the money is going directly to my US account, would I still need to file an FBAR? I won't actually have a foreign account at all in this transaction - the buyer is wiring the money directly to my account in America.

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23 You're right that if the money goes directly to your US account and you never have it in a foreign account, you wouldn't trigger FBAR requirements based on this specific transaction. However, be careful about any other foreign accounts you might have, even temporarily. For example, if you have a foreign account set up to handle any aspect of the sale closing, or if there's an escrow account in the foreign country that you have signature authority over, even briefly, that could potentially trigger FBAR requirements if the amount exceeds $10,000.

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4 Has anyone dealt with property in a country that doesn't have a tax treaty with the US? I sold land in Brazil and ended up paying taxes in both countries without any offset. It was a financial disaster.

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16 You might have missed something. Even without a tax treaty, you can usually claim a Foreign Tax Credit on Form 1116 for taxes paid to foreign governments on the same income. Did your tax preparer look into this? It doesn't eliminate all double taxation but should have reduced your US tax liability.

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Liam McGuire

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One approach I've seen work well is electing to have your LLC taxed as an S-Corporation instead of a sole proprietorship. This creates a separate tax entity where you can implement an accountable plan for vehicle reimbursement that can be more advantageous than the straight mileage deduction. The key is proper documentation and separation between business and personal use. No matter what approach you take, you NEED to keep detailed mileage logs. The IRS routinely disallows vehicle deductions during audits because of poor record keeping.

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Amara Eze

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Can you explain more about this accountable plan thing? I've never heard of it but sounds like it might be useful for my situation. My LLC is taxed as an S-corp already.

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Liam McGuire

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An accountable plan is an arrangement that allows your business to reimburse you for business expenses without those reimbursements being counted as taxable income to you. For it to qualify, you need three key elements: a business connection for the expense, adequate accounting within a reasonable time period, and returning excess reimbursements. For vehicles specifically, you can set up a plan where your S-Corp reimburses you at the standard IRS mileage rate for documented business miles. This creates a deductible business expense for the company while providing you tax-free reimbursement. It's often more advantageous than trying to deduct lease payments directly, especially for mixed-use vehicles.

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Has anyone tried just buying the car personally and then just billing your LLC for mileage at the IRS rate? I think its like 67 cents per mile now? Seems way simpler than all this lease stuff.

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Thats what i do! way easier and no headaches about mixed use. I just keep track of business miles in an app and bill my LLC monthly. My accountant said its the cleanest way to do it for a small business owner.

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