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Ask the community...

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Paolo Longo

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The IRS Authentication Protocol for in-person verification requires biographic verification (your ID) and residential verification (proof of address). The standard procedure allows for documentation discrepancies if you can provide supplementary evidence. A utility bill, bank statement, or lease agreement with your current address should suffice as secondary verification. The verification threshold is typically met with two concordant documents, even if your primary ID shows a different address.

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Mei Chen

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I went through this exact situation in January 2024! My driver's license showed my old college address but I filed my return with my current work address. The verification agent was completely understanding - they see this all the time, especially with young professionals who move frequently. I brought my lease agreement, two utility bills, and a bank statement all showing my current address. The agent barely blinked at the mismatch and said "happens every day." The whole appointment took maybe 20 minutes. One tip: organize your documents beforehand in a folder - it shows you're prepared and makes the process smoother. Don't stress about this, you'll be fine!

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Nina Chan

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I went through something very similar when I switched jobs mid-year and my new employer somehow set up my withholding incorrectly. The good news is that with 2 kids under 10, you have some solid tax credits working in your favor. The Child Tax Credit alone could give you up to $4,000 ($2,000 per child), and depending on your income level, a significant portion of that can be refundable even if you paid zero in withholding. The Earned Income Tax Credit could also apply if your income falls within certain ranges - with 2 qualifying children, this can be worth thousands more. Your health issues might also qualify you to file as Head of Household, which has better tax brackets and a higher standard deduction. I'd definitely recommend running your numbers through some tax software to get a realistic picture, but don't panic - families with dependents often come out better than they expect, even with withholding issues.

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NightOwl42

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This is really reassuring to hear from someone who's been through it! I'm definitely going to look into the Head of Household filing status - I hadn't even considered that might apply to my situation. The potential refund amounts you mentioned sound way better than I was expecting. Do you remember roughly what income range qualifies for the full Earned Income Tax Credit with 2 kids? I want to get a better sense of where I might fall.

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The EITC income limits for 2023 (filing in 2024) with 2 qualifying children are pretty generous - you can earn up to about $50,594 if filing single or $56,844 if married filing jointly and still get some credit. The maximum EITC with 2 kids is $6,164, which phases out as your income increases. Combined with the Child Tax Credit, you could potentially see a substantial refund even with zero withholding. Just make sure your kids meet the qualifying child requirements (age, relationship, residency tests) and that they have valid Social Security Numbers. Also, definitely fix your W-4 going forward to avoid potential underpayment penalties next year. Your situation with health issues and being the primary caregiver for 2 young kids sounds like it would qualify you for Head of Household status, which would give you even better tax treatment.

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This is exactly the kind of detailed breakdown I was hoping to find! The EITC income limits you mentioned are really helpful - it sounds like there's a decent chance I could qualify for at least some of that credit based on my current income situation. I'm definitely going to look into the Head of Household status too since I am the primary caregiver. One quick question - when you mention "underpayment penalties," is that something that would apply to this tax year since I've already had no withholding for most of it, or is it more about making sure I fix things going forward? I'm trying to figure out if I should be worried about penalties on top of whatever I might owe.

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Anna Kerber

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I was in your exact position last year! Went with forming my own business (LLC taxed as S-Corp) rather than taking the 1099 contractor role and the tax savings have been significant. Two HUGE things to know: 1) Health insurance - as an S-Corp owner, you can have your business pay for your health insurance (it's deductible for the business) but you have to report it as income on your W-2. Still better than paying with post-tax dollars! 2) Home office deduction is a PAIN to calculate but worth it. If you go S-Corp route you need to have an "accountable plan" to reimburse yourself for the home office. Making estimated quarterly tax payments is annoying but once you get systems in place its not too bad. Good luck!

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Niko Ramsey

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Im considering the same but worried about all the extra paperwork. How much extra time do you spend on admin/accounting stuff each month compared to when you were an employee?

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Ashley Adams

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Great question! I faced a similar decision two years ago and went with the small business route. Here's what I learned that might help: The $20k income difference you're projecting might actually be smaller when you factor in taxes. As a 1099 contractor at $85k, you'd pay self-employment tax on the full amount. With your own business, you have more flexibility with business expenses that can reduce your taxable income. One major consideration: client diversification. That $85k contract sounds great until it ends. I started my freelance business at $68k first year but by year two I was at $95k with multiple clients. The security of diverse income streams has been worth more than the initial pay cut. Don't forget about business credit building - having your own business lets you establish business credit separate from personal, which can be valuable for future growth and equipment purchases. My recommendation: if you're confident in your marketing skills and have some initial clients lined up, the business route gives you more long-term upside and tax flexibility. The 1099 role could be a good stepping stone to build skills and save up before launching your own thing.

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This is really valuable perspective! The client diversification point is huge - I hadn't fully considered how risky it could be to have 100% of my income from one source. Quick question: when you say you have more flexibility with business expenses to reduce taxable income, are there specific expenses that work better with your own business vs 1099 contracting? I'm trying to understand if the deductions are actually different or if it's more about having better documentation/justification for expenses when you have multiple clients.

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Emma Swift

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One thing I haven't seen mentioned yet is the importance of keeping your LLC's investment activities clearly documented and separate from any personal trading you might do. Even though both end up on your personal Schedule D for a disregarded entity, you'll want to maintain clear records showing which transactions were made through the LLC versus any personal accounts. This becomes especially important if you have both LLC and personal investment accounts with the same brokerage. I'd recommend using separate brokerages if possible, or at minimum keeping very detailed records that clearly identify the source of each transaction. If you ever get audited, the IRS will want to see that you maintained proper separation between your business and personal activities, even though they're taxed the same way. Also, since you mentioned your accountant disappeared, you might want to consider finding a new CPA before next year's tax season starts. Having professional guidance becomes even more valuable as your LLC grows or if you start generating more complex investment income. The peace of mind is worth the cost, especially when dealing with business entity taxation rules that can change or have nuances you might miss filing on your own.

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Ravi Patel

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This is excellent advice about maintaining separation between LLC and personal investment activities! I learned this lesson when I had to reconstruct my records for an IRS inquiry a few years back. Even though everything ultimately flows to your personal return, the IRS still expects you to be able to clearly demonstrate which activities belonged to which "bucket." I'd also add that if you're planning to continue investing through your LLC, consider setting up a completely separate accounting system or at least dedicated spreadsheets to track the LLC's investment performance separately from any personal trading. This makes it much easier at tax time and provides the documentation trail you'd need if questions ever arise. Your point about finding a new CPA is spot-on too. While DIY tax software has gotten pretty good, having a professional who understands entity taxation can save you from costly mistakes and help with tax planning strategies you might not know about. The cost of a good accountant is usually far less than the potential penalties or missed opportunities from going it alone, especially as your business and investment activities become more complex.

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One additional consideration I haven't seen mentioned yet is the potential impact on your LLC's operating agreement if you're doing significant investment activity. While the tax treatment for a disregarded entity is straightforward (everything flows to your personal return), you'll want to make sure your operating agreement properly addresses investment activities if that wasn't originally contemplated when you formed the LLC. Some operating agreements are written very narrowly and might not explicitly allow for investment activities beyond the LLC's primary business purpose. If you plan to continue trading through the LLC, it's worth having an attorney review your operating agreement to ensure it gives you the authority to engage in investment activities and that any liability protections you're seeking are properly structured. Also, depending on the volume and frequency of your trading, you might want to consider whether you need to register for any additional business licenses or comply with securities regulations in your state. Most casual investing doesn't trigger these requirements, but if you're doing substantial trading activity through a business entity, there could be additional compliance considerations beyond just the tax reporting we've been discussing. Better to address these structural issues now while your investment activity is relatively new rather than trying to fix them later if your trading becomes more substantial or complex!

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Amara Eze

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This is a really important point that I hadn't considered! I just reviewed my LLC operating agreement after reading your comment and realized it only mentions my consulting business activities - nothing about investments or securities trading. Since I've been doing some stock trading through the LLC this year, I'm now wondering if I need to amend the operating agreement to explicitly allow investment activities. Do you know if there are any risks to having investment activities that aren't specifically covered in the operating agreement? Could this potentially affect the liability protection that the LLC is supposed to provide? I'm definitely going to look into having an attorney review this, but I'm curious if anyone else has dealt with this situation. It seems like something that could easily be overlooked when you're just focused on getting the tax reporting right.

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This comparison is incredibly helpful! I've been a TurboTax user for about 12 years and have watched the prices creep up year after year. Last season I paid around $160 for Premier plus state filing, and honestly started questioning whether I was getting my money's worth. Your identical results test is exactly the validation I needed to feel confident about switching. I have a fairly similar tax situation - two W-2s, mortgage interest, some education credits for my kids, and a small amount of stock activity. If FreeTaxUSA can handle all of that for under $15, it's a no-brainer. One thing that's always made me stick with TurboTax is their guarantee that they'll pay any penalties if there's an error in their calculations. Does FreeTaxUSA offer anything similar? I know the math should be the same, but that peace of mind has been worth something to me over the years. Really looking forward to your multi-platform comparison next year! Having someone actually test these side-by-side with real data is so much more valuable than just reading marketing materials from each company.

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Emma Wilson

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Great question about the guarantee! FreeTaxUSA does offer an accuracy guarantee - they'll cover any IRS penalties and interest that result from calculation errors in their software, plus they'll pay for a tax professional to help resolve the issue. It's similar to TurboTax's guarantee in terms of covering penalties from their mistakes. The main difference is in the level of support offered during the resolution process. TurboTax tends to provide more hand-holding if issues arise, while FreeTaxUSA's approach is more straightforward - they'll make you whole financially but expect you to be more self-sufficient in working through any problems. Given that you have a similar tax situation to the original poster, I'd say the guarantee difference is minimal compared to the $145+ in annual savings. Most calculation errors that would trigger penalties are extremely rare with any established tax software since they all use the same IRS tax tables and formulas. Looking forward to seeing more detailed comparisons next year too! This kind of real-world testing is so much more helpful than trying to parse through marketing claims from different companies.

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Mei Chen

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Thank you so much for this detailed comparison! As someone who's been using TurboTax for years without really questioning the cost, your side-by-side test is exactly what I needed to see. The fact that you got identical results for $14.99 vs $188 is absolutely mind-blowing. I have a similar tax situation with multiple income sources and some investment activity, so I'm definitely going to try FreeTaxUSA next year. The idea of doing a parallel comparison like you did is brilliant - it gives you the confidence to switch while still having that safety net of verification. I'm also really intrigued by your plan to test multiple platforms including Cash App Tax and the IRS Free File options. Having someone actually put these through real-world testing with the same data will be incredibly valuable for this community. One question - did you notice any differences in how long each platform took to complete? Sometimes the cheaper option can be more time-consuming, so I'm curious if that was a factor in your experience. Looking forward to your expanded comparison next year! This thread has already given me several alternatives to research before next tax season.

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