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Ask the community...

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GalaxyGlider

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Have you considered making an extra payment to your student loans if you have any? Interest on student loans is deductible up to $2,500 depending on your income, though with your household income you might be phased out of this deduction. Also, if either of you is self-employed or has any 1099 income, you could make business purchases you were planning for early 2024. New computer, office equipment, professional subscriptions, etc.

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We don't have any student loans left fortunately, but my wife does have some consulting income on top of her regular job. That's a great idea about accelerating some business purchases - she was planning to upgrade her home office setup in January anyway. Is there a minimum amount of 1099 income needed to make this worthwhile?

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GalaxyGlider

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There's no minimum threshold for 1099 income to take business deductions. As long as your wife's consulting work is a legitimate business activity (not just a hobby), she can deduct ordinary and necessary business expenses against that income. Since she was already planning the office upgrade, accelerating it into 2023 makes perfect sense. Just make sure the purchases are actually made and put into service before December 31st - ordering isn't enough, you need to receive and start using the items this year. Keep excellent records of the purchases and how they relate to her consulting work.

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Has anyone mentioned charitable donations yet? With your income level, this could be a significant tax saver. If you normally give to charity, consider bunching multiple years of donations into 2023. You could also look into a donor-advised fund - you get the full tax deduction this year but can distribute the money to charities over future years.

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Donor-advised funds are amazing for tax planning! We did this last year and it worked great. You can even donate appreciated stock directly to the fund and avoid capital gains taxes completely while still getting the full deduction.

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Micah Trail

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You should check if both W-2s are using the correct filing status and withholding allowances. Sometimes when you switch payroll systems, your W-4 information doesn't transfer correctly. I had this same issue last year when my company switched from ADP to Paychex. Make sure both payroll processors have the same W-4 information. Also, if you have any other income (investments, side gigs, etc.) that could be pushing you into a higher bracket too.

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Danielle Mays

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That's a good point, I hadn't thought about that! When we switched payroll systems, I don't think I filled out a new W-4 for the second one - they might have just used default withholding which would explain the issue. Do you think it's worth asking my HR department if I can see what withholding settings they had for me on both systems?

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Micah Trail

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Absolutely ask your HR department! They should be able to tell you exactly what withholding instructions they had on file for each system. Default withholding typically assumes you're single with no dependents and only one job, which often results in underwithholding if that's not your situation. I'd recommend getting copies of both W-4s they have on file, then filling out a new one with the correct multiple job calculations. The IRS has a good tax withholding estimator on their website that can help you get it exactly right for your situation.

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Nia Watson

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Has anyone else noticed that payroll systems are TERRIBLE at calculating withholding when you have multiple jobs or income sources? This is like the 3rd post I've seen about this same issue. The whole system seems designed to make people mess up and owe money.

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It's not really that payroll systems are terrible - they're doing exactly what they're designed to do. The problem is they only know about the income they're processing. It's actually on us to tell our employers to withhold extra when we have multiple income sources.

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Nia Watson

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That makes sense, but it still feels like the system is unnecessarily complicated. Like why can't the IRS just figure out how much I should be paying based on what I made last year and tell my employers? Seems like they deliberately make it confusing so people mess up and they collect penalties.

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Jessica Nolan

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Has anyone tried TaxSlayer? I hear it's cheaper than TurboTax but not sure if it's any better interface-wise.

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TaxSlayer is ok but I found it confusing for itemized deductions. Kept getting different numbers than I expected and couldn't figure out why.

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Jessica Nolan

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Thanks for the info! I'll probably try FreeTaxUSA based on all the recommendations here. The dated interface doesn't bother me as much as TurboTax's constant upselling. I appreciate the heads-up about the itemized deduction issues. I don't itemize anymore with the higher standard deduction, so hopefully that won't be a problem for me.

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I switched to H&R Block Online last year from TurboTax and found it much more straightforward! It lets you jump directly to forms and has less upselling. Might be worth checking out too.

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How much did you end up paying for H&R Block compared to TurboTax? And did you find it easier to navigate? My main frustration is just wanting to directly enter my forms without going through their "life changes" questionnaire every time.

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I paid about $70 for H&R Block's Deluxe version compared to $120 I was paying for TurboTax. It was definitely easier to navigate - they have a "forms mode" that lets you go directly to specific forms without going through all the interview questions first. You can still use the interview mode if you want guidance, but it's completely optional. The interface feels less cluttered too, and I didn't get constant popups trying to upgrade me to more expensive versions.

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Ryder Ross

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I'm a retail trader who does about 500-1000 trades per year, and I've never paid per-transaction fees. That's absolutely ridiculous. I use FreeTaxUSA and just import my CSV files from my brokers. Total cost? $15 for the software. Even if you don't want to DIY, most CPAs I've talked to charge a flat $100-200 additional fee for Schedule D reporting, regardless of transaction count. Your preparer is trying to make a killing off you because they think you don't know better. For 2020 specifically, those COVID credits are pretty valuable, so definitely file, but find someone charging a reasonable rate!

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Ally Tailer

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Did you have to do anything special with FreeTaxUSA for options trades specifically? I've heard they're treated differently than regular stock transactions for tax purposes and want to make sure I'm doing it right.

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Ryder Ross

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For options in FreeTaxUSA, you just need to make sure your import file correctly identifies them as options contracts with the right expiration dates and strike prices. The software handles the different tax treatment automatically. One thing to watch for is that some brokers (especially Robinhood back in 2020) sometimes didn't properly classify certain spreads or multi-leg option strategies in their export files. If you did any complex options strategies, you might need to double-check those specific entries, but for simple buys and sells it works perfectly without any special steps.

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Dealt with this exact issue for my 2020 filing. I found a middle ground by asking my CPA to just charge me their hourly rate instead of per transaction. Ended up paying around $400 total for a return with 300+ trades since I had everything organized from my brokers already. Maybe ask your preparer if they'd consider an hourly rate alternative? If they refuse, that's a red flag that they're just trying to milk you for cash.

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Henry Delgado

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This is the way. I'm a bookkeeper (not tax professional) and NO reasonable preparer should be charging per transaction when software can import these in bulk. Either hourly or a reasonable flat fee is standard practice for high-volume traders.

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Another option you should look into is the "qualified principal residence indebtedness" exclusion if this was related to your primary home, or the "qualified farm indebtedness" exclusion if it was farm-related debt. Different exclusions apply in different situations, and it's important to use the right one on Form 982. Also, make sure that the 1099-C is legitimate. Sometimes debt collectors send these forms for debts that are past the statute of limitations, which can be problematic. If the debt is really 11-12 years old, you might want to verify that the 1099-C was properly issued.

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Zoey Bianchi

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Thanks for mentioning this, but my 1099-C is definitely for an old credit card debt, not a home mortgage or farm debt. It was from a major bank that I definitely had an account with back then, so I think it's legitimate. The weird thing is why they waited so many years to cancel it and send the 1099-C. Is there a time limit on when they can issue these forms? The debt was from around 2012, but they just cancelled it in 2023.

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There's actually no time limit on when creditors can issue a 1099-C after cancelling a debt. They're required to issue it for the tax year in which they actually cancel the debt, regardless of how old the original debt was. In your case, even though the debt originated in 2012, if the creditor officially cancelled it in 2023, then that's when the taxable event occurred. This is fairly common with old debts that have been sitting in collections for years. The good news is that insolvency is still an option regardless of how old the original debt was. Focus on your financial situation at the time of cancellation (2023) when determining if you qualify for the insolvency exclusion.

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one thing nobody mentioned yet is that if u qualify as insolvent, u need to reduce certain tax attributes like NOL, credit carryovers etc. on that form 982. its in part 2 of the form. most ppl dont have these but if u do its important. also dont forget to actually attatch form 982 to your return! if ur e-filing the software should do this for u but double check.

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Ethan Scott

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That's a great point. Most people filing basic returns won't have these tax attributes, but it's an important consideration if you have a more complex tax situation. Also worth noting that if you're using free tax filing software, some of them don't support Form 982. You might need to upgrade to a paid version to properly handle the insolvency exclusion.

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