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Ask the community...

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  • DO NOT post call problems here - there is a support tab at the top for that :)

Miguel Harvey

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One important thing nobody's mentioned yet - if you file jointly, you're BOTH responsible for the entire tax bill and any potential errors on the return. Sometimes filing separately makes sense if one spouse has sketchy tax situations, tons of self-employment income with questionable deductions, or past tax problems. Also, if either of you has income-based student loan payments, filing jointly might increase those payments since they'll be based on your combined income. Something to consider if you or your fiancΓ©e has significant student debt.

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Ashley Simian

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What about medical expense deductions? My husband has a lot of medical costs but I don't. Does filing jointly or separately matter for that?

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Miguel Harvey

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Medical expense deductions are definitely impacted by filing status. For 2025, you can only deduct medical expenses that exceed 7.5% of your adjusted gross income (AGI). If you file separately, only your husband's medical expenses and AGI would be considered for his return. Here's a simple example: If your husband's AGI is $40,000 with $10,000 in medical expenses, and yours is $80,000 with minimal medical expenses, filing separately would let him deduct anything over $3,000 (7.5% of $40,000). So he could deduct $7,000. But filing jointly with a combined AGI of $120,000 means you'd only deduct expenses over $9,000 (7.5% of $120,000), reducing your deduction to just $1,000. In cases with large medical expenses, running calculations both ways is definitely worth it.

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Oliver Cheng

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Does anyone know if paying for TurboTax is worth it when you're married? The free version doesn't let you itemize deductions which seems important for homeowners, but the paid versions are like $100+. Are there better options for couples who want to make sure they're making the right filing choice?

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Taylor To

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I've used FreeTaxUSA for the last few years - it's free for federal and like $15 for state. It handles all the married filing jointly stuff perfectly and lets you compare filing jointly vs separately to see which saves more. WAY cheaper than TurboTax and does basically everything the paid version does.

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Andre Dupont

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Something nobody's mentioned yet - if your mother-in-law is from Canada, check if there's a tax treaty that might affect this situation. Some treaties have specific provisions about dependents and what counts as "residency" for tax purposes.

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Do you know where I can find info about tax treaties? My in-laws are from India and I've wondered about this too.

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Andre Dupont

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You can find tax treaties on the IRS website - search for "United States Income Tax Treaties A to Z" and you'll find a list of all countries with treaties. For more detailed information, look for IRS Publication 901 (U.S. Tax Treaties). For India specifically, there is a tax treaty, but dependency rules are complex. The treaty mainly covers things like double taxation of income, but personal exemptions and dependent status are usually determined by the regular IRS rules I mentioned earlier.

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Jamal Wilson

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If the mother visits from Canada for 8 months, wouldn't she technically be considered a US resident under the substantial presence test? That might change things completely.

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Mei Lin

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Good point! I think the substantial presence test is 183 days (about 6 months) in a calendar year, so at 8 months she'd likely meet that. Would that make her ineligible as a dependent?

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Adaline Wong

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For your vintage sales you might also qualify for what's called "Section 1244 Stock Loss" treatment depending on how you've structured things. When I was selling collectibles I found it helpful to keep a simple notebook with me so I could jot down what I paid right after buying things. Just noting the date, brief item description, and price paid. You might also want to take photos of items when you purchase them with any price tags visible. Even starting this practice now will help you next year. The tax code doesn't expect perfect documentation for every small purchase, but showing you have a systematic approach to tracking helps tremendously.

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Rajan Walker

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Thanks for the notebook tip - that's a great idea! I'll definitely start doing that. But what's this Section 1244 thing you mentioned? Is that something that would apply to my situation with just selling stuff online as a side thing?

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Adaline Wong

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I misspoke about Section 1244 - that's actually for losses on small business stock and wouldn't apply here. What I meant was that resellers can use the "Cost of Goods Sold" section on Schedule C to account for your inventory costs. The notebook method works great for casual sellers. I recommend categorizing items by type and condition, which helps establish a pattern. For example, "vintage t-shirts - good condition - $3-5 each" or "collectible figurines - mint condition - $10-15 each." This creates a reasonable framework for your estimates. Starting this practice now will make next year's taxes much easier, and having some documentation is always better than none.

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Gabriel Ruiz

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Has anyone used TurboTax for reporting 1099-K for their casual sales? I'm in a similar situation and wondering if it walks you through estimating costs properly or if I need something more specialized.

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TurboTax works ok for this but isn't great. It asks for cost of goods sold as a total number rather than helping you itemize. I found FreeTaxUSA actually handled my small eBay business better and asked more relevant questions about inventory and costs. Plus it's way cheaper.

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Peyton Clarke

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I used TurboTax last year for my Etsy 1099-K. It was decent but I had to manually create my own spreadsheet for tracking cost of goods sold. It doesn't really help with estimating costs when you don't have receipts - you just enter your total estimate. If you're worried about documentation, you might want something more specialized or at least create your own tracking system alongside TurboTax.

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Can I claim my girlfriend and her child as dependents? Complex custody situation inside...

I've got a somewhat complicated situation that I'm trying to figure out for tax filing. My girlfriend didn't work at all this year as she stayed home with our newborn daughter. I'm planning to claim our daughter as my qualifying child and my girlfriend as a dependent. The tricky part involves my girlfriend's son from a previous relationship. He lived with us 5-6 nights per week from January through June, then moved in with us full-time (100%) from July through December. The courts granted my girlfriend a temporary parenting plan making her the custodial parent, and her ex currently has zero visitation rights due to a protection order we had to take out against him. Here's what I'm wondering based on these facts: 1. Since my girlfriend had no income and won't be filing, she won't be claiming her son. I'll be claiming her as my dependent. 2. My understanding is that since my girlfriend is the custodial parent, her ex would need her permission to claim their son, which she absolutely isn't giving. 3. Her ex didn't come close to providing half of the boy's financial support, and the child didn't live with him for anywhere near half the year. So I don't think he qualifies to claim the child anyway, right? Given all this, am I eligible to claim her son as my dependent? And even if I can't claim him, is there any possibility her ex could claim him despite only having him for a few days during the first half of the year? Any insights would be super helpful. This tax situation is giving me a headache!

Drake

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One important thing I haven't seen mentioned yet - make sure you keep ALL documentation about the custody situation! If the ex tries to claim the child (which happens a lot in these situations), both returns will get flagged and you'll need to prove your case. Documents you should keep: - Copy of the court order showing custody - School records showing the child's address - Medical records you've paid for - Documentation of support you've provided (receipts for clothes, food, etc.) - The protection order documentation - Calendar or records showing the actual days the child was in each home The IRS will side with whoever files first initially, then you'll have to prove your case if there's a dispute. With a court order though, you're in a strong position.

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Thanks for this detailed list! We actually have most of these documents already because of the custody situation. The court order is definitely the strongest piece, but I hadn't thought about keeping a calendar of the actual days. That's really smart, especially for the first half of the year when he was with us most nights but not all. Do you know if there's a specific form I need to fill out to claim him since he's not my biological child? Or do I just list him as a dependent when filing?

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Drake

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You'll list him as a dependent on your tax return just like you would any other dependent. There's no special form required specifically because he's not your biological child. The regular dependency forms (Form 1040 and the associated schedules) are all you need. When you're entering his information in your tax software or forms, you'll need to specify your relationship to him. Since he's not related to you by blood or marriage, you would typically select "Other" and might need to write in something like "girlfriend's child" or "member of household" depending on the tax software you're using.

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Sarah Jones

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Has anyone mentioned the Child Tax Credit yet? If you can claim the girlfriend's son as your dependent, you might qualify for the Child Tax Credit which is worth up to $2,000 per qualifying child! That's a significant tax benefit. Just make sure you have his Social Security Number. The IRS requires this for claiming the Child Tax Credit.

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You also might qualify for the Earned Income Credit if your income is within the eligible range. Having two qualifying children (your daughter and potentially your girlfriend's son) could significantly increase that credit compared to just claiming one child.

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Have you looked into a disclaimer? In some cases, you can execute a qualified disclaimer of inheritance, which essentially says "I don't want this money" and it passes to the next eligible recipient. This has to be done within 9 months of death, and you can't have "accepted" the benefit (which might be an issue if you've already rolled it into your 401K). If the rollover is recent, talk to the plan administrator about possibly unwinding it, then execute a disclaimer. This might allow the money to go directly to her brother without passing through you.

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Yuki Yamamoto

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I think I've already missed that window since it's been about 11 months since her passing, and as you mentioned, I've already completed the rollover into my 401K. I feel like I should have researched this better before making the initial decision, but I was dealing with a lot emotionally and just followed what the HR person at her company suggested.

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That's understandable - these decisions often need to be made during difficult emotional times. Since the disclaimer option is no longer available, your best approach now is probably a combination strategy: First, designate her brother as the beneficiary for that portion of your 401K, ensuring he'll receive it if something happens to you. Then, work out a yearly gifting strategy once you're eligible for qualified distributions without penalties. You might also consult with an attorney about creating a simple agreement documenting your intentions, which could help clarify things for your own estate planning. Don't be too hard on yourself - you're trying to do the right thing in a system that doesn't make it easy.

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Check if your 401K plan allows for hardship withdrawals or loans. You could potentially take a loan from your 401K (typically up to 50% of the balance or $50,000, whichever is less), then use those funds to gift to the brother without the early withdrawal penalty. You'd have to repay the loan with interest, but the interest goes back into your account so you're essentially paying yourself.

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NeonNova

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This is actually not great advice. 401K loans become immediately due if you leave your job, and since OP is living overseas, that could be risky. Plus, if you can't repay the loan, it becomes a distribution with all the taxes and penalties. The gift tax concerns would still apply too.

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