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Justin Evans

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I went through something similar last year and here's what worked for me. The most important thing is to understand that as the custodial parent, you have the strongest legal claim to your children as dependents, even with the grandmother living in the same house. First, file your taxes as early as possible in January. The IRS doesn't actually give preference to who files first, but if your return is already processed, it makes things much cleaner. For the grandmother situation specifically - since you live together, you'll need to be able to prove you provide more than 50% of your children's total support. Start documenting everything NOW: keep receipts for groceries (estimate the portion for your kids), their clothing, medical expenses, school supplies, etc. Even if grandma pays utilities, if you're covering the majority of kid-specific expenses plus your share of housing, you should easily meet the support test. The father has zero legal ground to stand on since the kids haven't lived with him since 2012. The IRS requires children to live with the claiming parent for more than half the year. I'd suggest having honest conversations with both of them about your intentions to claim the kids. Sometimes people don't realize they're not legally entitled to claim children, and a polite explanation can prevent the whole mess. With grandma, maybe you can work out an arrangement where you contribute more to household expenses with part of your refund. If anyone does file claiming your kids, don't panic. File a paper return with your documentation, and the IRS will apply their tiebreaker rules - which strongly favor you as the biological parent who lives with the children.

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This is really helpful! I'm wondering about the documentation process - when you say to estimate the portion of groceries for the kids, how detailed does that need to be? Like, do I need to go through every receipt and calculate what percentage was for kids' food versus adult food, or is a reasonable estimate okay? Also, you mentioned filing early in January - does the IRS actually start accepting returns right away, or do they wait until a certain date? I want to make sure I'm not just sitting there waiting when I could be getting this filed and protected. One more question - if I do end up in a dispute situation where someone else claims my kids first, how long does it typically take for the IRS to sort it out? I'm worried about not getting my refund for months if this becomes a mess.

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Brooklyn Foley

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Great questions! For the grocery documentation, a reasonable estimate is totally fine - the IRS isn't expecting you to itemize every apple and box of cereal. I kept a simple log for a few months tracking roughly what I spent on kid-specific items (their snacks, school lunches, etc.) versus general household groceries, then used that percentage for the rest of the year. Something like "approximately 40% of grocery expenses attributable to children's food" with some supporting receipts is sufficient. The IRS typically starts accepting returns in late January (around January 23rd this year, but check their website for exact dates). You can prepare and submit your return before then through tax software, and it'll be transmitted as soon as they start processing. Regarding dispute timelines - this varies, but typically takes 8-16 weeks once the IRS identifies duplicate dependent claims. They'll send letters to both parties requesting documentation. The good news is that as the custodial parent with proper documentation, you should win any dispute. Some people get their refund processed normally even with a dispute if their documentation is solid from the start. Pro tip: when you file, include a statement with your return explaining your living situation and your role as primary caregiver. This can help avoid questions later. Something like "Children reside with taxpayer (mother) at same address as paternal grandmother, but taxpayer provides majority of support and care.

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Sara Hellquiem

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I understand how stressful this situation must be! You're dealing with multiple people who might try to claim your children, but the good news is that as their custodial parent, you have the strongest legal position. Here's my advice as someone who's navigated similar family tax issues: **Immediate steps:** 1. **Start documenting everything NOW** - Keep receipts for groceries (even a rough estimate of what goes to feeding your kids), their clothing, medical bills, school expenses, etc. Even though you live with grandma, if you're providing the majority of your children's support, you have the right to claim them. 2. **Have those difficult conversations** - Talk to both the father and grandmother before tax season hits full swing. For the father, explain that since the kids haven't lived with him since 2012, he legally cannot claim them under IRS rules. For grandma, acknowledge that you appreciate her help but as their parent, you need these tax benefits to continue supporting them. 3. **File early** - The IRS usually starts accepting returns in late January. Get your return prepared and submit it as soon as possible. **If disputes arise:** Don't panic if someone else files first. You can still file a paper return claiming your children, and the IRS will apply their tiebreaker rules. As the biological parent who lives with and supports the children daily, you should prevail in any dispute - just make sure you have that documentation ready. Consider getting a signed statement from grandma acknowledging that you're the primary provider for the kids. This could be invaluable if questions come up later. You've got this - just stay organized and proactive!

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This is such solid advice! I especially like the point about getting a signed statement from grandma - that could really save headaches down the road. One thing I'd add is to maybe also keep a simple calendar or log showing which days your kids are with you versus anywhere else. Since the IRS uses that "more than half the year" test, having a clear record could be helpful. Even just noting on a regular calendar when they sleep at your house, go to school from your address, etc. Also, when you have that conversation with the father, you might want to do it via text or email so you have written proof that you told him the kids live with you and that you'll be claiming them. Sometimes people conveniently "forget" these conversations later when tax time rolls around!

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This thread has been incredibly helpful! As someone who's been buying and selling vintage collectibles for a few years now, I can confirm everything that's been said about the collectible tax rates. One additional point that might be useful - if you're dealing with multiple collectibles sold throughout the year, you might want to consider bunching your sales into years when your overall income is lower. Since collectibles are taxed at your ordinary income rate (capped at 28%), strategic timing can really make a difference. For example, I had a big bonus year where I was temporarily in the 32% bracket, so I held off selling some collectibles until the following year when I was back down to 24%. Saved me 4% on the gains, which added up to real money. Also, if you're serious about collecting comics or other items as investments, consider keeping a detailed log of market research, time spent researching purchases, and any educational materials you buy about collecting. While you can't deduct these as business expenses if you're treating it as investment activity, having detailed records shows the IRS that you're approaching this seriously as an investment rather than just a hobby.

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CosmicCaptain

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This is such great strategic advice about timing the sales! I never thought about how my overall income in a given year could affect the tax rate on collectibles. That 4% difference you saved really shows how much planning ahead can matter. Your point about keeping detailed records of research and education is smart too. Even if you can't deduct those expenses, showing that you're approaching collecting systematically rather than just casually buying things you like could definitely help if the IRS ever questions whether it's investment activity versus a hobby. Question for you - when you say "bunching sales," do you mean literally waiting until January of the following year, or is there more nuance to the timing? I'm wondering if there are other factors like estimated tax payments that might complicate the strategy of shifting income between tax years.

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Dmitry Ivanov

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Great question about comic books! I've been collecting and occasionally selling comics for about 5 years now, and your understanding is spot on. The collectible capital gains rate is indeed your ordinary income tax rate capped at 28%. One thing I'd add that hasn't been mentioned much - make sure you understand what constitutes your "basis" in the comics. It's not just what you paid for the comic itself. You can also include: - Shipping costs when you bought them - Sales tax you paid - Professional grading fees (CGC, CBCS, etc.) - Authentication costs - Any restoration work (though this can be tricky territory) I learned this the hard way when I sold a key Silver Age comic last year. I had paid $800 for it, plus $50 shipping, $30 grading fee, and about $15 in sales tax. So my basis was $895, not just the $800 purchase price. When I sold it for $1,400, I only owed taxes on $505 in gains instead of $600. Also, keep digital copies of all your receipts and document the condition when you bought them. The IRS can be pretty particular about collectibles since values are often subjective. Having a paper trail makes everything much smoother if you ever get audited. Good luck with your comic collecting adventure! The vintage market has been really strong lately.

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This is exactly the kind of detailed breakdown I was hoping to find! Thank you for sharing your real-world example with the Silver Age comic - seeing the actual numbers makes it so much clearer how all those additional costs add up and reduce your taxable gain. I hadn't thought about including sales tax as part of the basis, but that makes total sense. Every little bit helps when you're trying to minimize the taxable gain. Your point about keeping digital copies of receipts is well taken too - I'm definitely going to start a dedicated folder for all comic-related expenses. One follow-up question: when you mention restoration work being "tricky territory," what do you mean exactly? Is it that some types of restoration might not qualify for inclusion in the basis, or is it more about the impact on the comic's authenticity and market value? Also, have you found any particular challenges with documenting the condition when you first bought comics, especially if you purchased them at conventions or local shops where you might not have as much formal documentation?

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Millie Long

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Great question about restoration! What I meant by "tricky territory" is that restoration can be controversial in the collecting community and can sometimes actually hurt a comic's value rather than help it. From a tax perspective, you can generally include restoration costs in your basis IF the restoration genuinely increases the item's value. But you need to be careful because some types of restoration (like color touch or trimming) are frowned upon by collectors and might make the comic worth less than if you'd left it alone. For documenting condition at purchase, I've started taking photos with my phone immediately when I buy comics, especially at conventions. I also try to get some kind of receipt or invoice, even if it's just a handwritten one from the dealer. Many convention dealers now use Square or similar systems that can email you a receipt. For local shops, I always ask for a receipt and make notes on it about the condition if it's not obvious. One trick I learned: if I'm buying something valuable without a formal grade, I'll sometimes write a brief condition description on the receipt right there at the time of purchase ("VF/NM, small crease upper right corner" or whatever). It helps establish the condition contemporaneously rather than trying to remember it months or years later when I sell.

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Leila Haddad

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Just wanted to add another perspective on the business structure aspect. Since your wife would be the owner of the B&B as a NZ citizen, you'll also need to consider whether this creates any issues with US gift tax rules if you're contributing funds to a business you don't legally own. Also, regarding the rental property in the US - even if you're breaking even cashflow-wise, don't forget that you'll be taking depreciation deductions which will reduce your basis. When you eventually sell, you'll have depreciation recapture to deal with, which is taxed as ordinary income up to 25%. This could create a significant tax bill down the road that many people don't anticipate. One more thing to research: NZ has something called the "bright-line test" for property investments, which could affect the tax treatment of your B&B if you sell within a certain timeframe. Since you're planning to reinvest profits initially, this might not be immediate concern, but it's worth understanding for long-term planning. The international tax situation is definitely complex, but with proper planning and the right resources, it's totally manageable. Good luck with the move!

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This is exactly the kind of detailed analysis I was hoping to find! The gift tax implications of contributing to a business I don't own is something I hadn't even considered. Would structuring it as a loan to my wife potentially avoid those issues, or would that create other complications? Also, the depreciation recapture point is really important - I was only thinking about the annual cash flow but you're right that the tax implications when we eventually sell could be substantial. Do you know if there are any strategies to minimize that impact, like 1031 exchanges for rental properties owned by expats? Thanks for mentioning the NZ bright-line test too. It sounds like there are tax implications on both sides that could really add up if we're not careful with the planning.

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Jamal Brown

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Great questions! For the gift tax issue, structuring contributions as a loan could help, but you'd need to document it properly with formal loan agreements, market interest rates, and actual repayment terms. The IRS scrutinizes loans between spouses, especially when one spouse owns a business the other is funding. Regarding 1031 exchanges for expats - this gets tricky. You can still do like-kind exchanges, but the timing requirements (45-day identification, 180-day completion) become much harder to manage from abroad. Plus, if you're a NZ tax resident, NZ might not recognize the tax deferral and could tax the gain immediately, defeating part of the purpose. For depreciation recapture, one strategy is installment sales if you owner-finance the buyer, which spreads the recapture over multiple years. Another option is converting to your primary residence before sale (though you'd need to meet the 2-out-of-5-years test while abroad, which has its own complications). The NZ bright-line test is currently 10 years for most investment properties, so definitely factor that into your long-term planning. Between US depreciation recapture and potential NZ bright-line tax, the timing of any property sales becomes really important.

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Honorah King

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One more consideration for your move to NZ - make sure you understand the timing of when you become a New Zealand tax resident. NZ uses a combination of factors including days present, permanent place of abode, and center of vital interests. This matters because it determines when you start being subject to NZ tax on your worldwide income. If you're keeping your US house initially and spending time setting up in NZ, you might have a period where both countries could claim you as a tax resident. The US-NZ tax treaty has tie-breaker rules, but it's something to plan for carefully. Also, since you mentioned potentially applying for NZ citizenship eventually, be aware that this could complicate your US tax situation if you ever want to renounce US citizenship down the road. The IRS has an "exit tax" (covered expatriate rules) that can be quite punitive for high-net-worth individuals, and they look at your net worth and tax compliance history over the 5 years before expatriation. Not saying you'd want to renounce, but it's good to understand all the long-term implications as you make these decisions. The expat tax world has lots of moving pieces that interact in unexpected ways!

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Juan Moreno

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This thread has been incredibly helpful! As someone who just started doing gig work myself, I wanted to add one more resource that's been a lifesaver for me - the IRS Publication 334 (Tax Guide for Small Business). It's free on the IRS website and has a whole section specifically about self-employment income and deductions. What I found most useful is that it explains exactly what records you need to keep and for how long (spoiler: keep everything for at least 3 years). It also has examples of legitimate business deductions for delivery drivers that I hadn't thought of, like car washes if you clean your car specifically to maintain a professional appearance for customers. One thing I wish someone had told me earlier - consider opening a separate checking account just for your gig work earnings and expenses. It makes tracking so much easier come tax time, and if you ever get audited, having that clear separation between personal and business finances looks really professional to the IRS. Some banks even offer free business checking accounts for low-volume businesses. Also, for anyone worried about the complexity of filing taxes with gig income - TurboTax, FreeTaxUSA, and other tax software have specific sections for gig workers that walk you through everything step by step. You don't need to be a tax expert to get it right!

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Ravi Patel

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This is such great advice about the separate checking account! I'm just getting started with Doordash and was wondering about the best way to keep everything organized. Opening a dedicated account for gig work makes total sense - it would definitely make it easier to see exactly how much I've earned and spent on business expenses. Quick question about the car wash deduction you mentioned - how often can you reasonably deduct that? I feel like if I claimed a car wash every week it might look suspicious, but my car definitely gets messier doing deliveries than it would from just personal driving. Also, do you happen to know if things like air fresheners or seat covers specifically for keeping the car clean/professional for customers would be deductible too? Thanks for mentioning Publication 334 - I'm definitely going to check that out. It's nice to have an official IRS source rather than just relying on random articles online that sometimes contradict each other!

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@Ravi Patel Great questions! For car washes, the key is reasonableness and documentation. If you re'doing deliveries regularly say (3-4 times a week ,)then washing your car weekly or bi-weekly could be justified, especially if you re'delivering food and need to maintain cleanliness standards. Just keep receipts and maybe note in your records why the wash was necessary e.g., (car "wash after rainy delivery week or" monthly "professional appearance maintenance .")Air fresheners and seat covers specifically for customer-facing work would likely be deductible as legitimate business expenses, as long as you can show they re'primarily for business use. The IRS looks for expenses that are ordinary "and necessary for" your business - and keeping your car clean and professional for customers definitely fits that criteria. The separate checking account has been a game-changer for me. I direct deposit all my gig earnings there and pay for all business expenses gas, (car washes, equipment from) that same account. Makes it super easy to calculate net profit and I never have to dig through personal transactions looking for business expenses. Some credit unions offer free business checking with no minimum balance requirements if you re'worried about fees. Publication 334 really is the gold standard - it s'dry reading but having the official IRS guidance gives me confidence I m'doing everything correctly!

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Luca Greco

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I'm jumping into this conversation as someone who just went through this exact situation last tax season! The confusion about the $400 vs $600 thresholds is so common among new gig workers. Here's what I learned the hard way: you're absolutely right that Doordash only sends a 1099-NEC when you hit $600, BUT the IRS still expects you to report all income regardless. The $400 threshold for self-employment tax is completely separate from the 1099 reporting requirement. At $342.50, you're currently under both thresholds, so technically you wouldn't need to file for self-employment tax purposes if this is your only income. However, I'd strongly encourage you to start tracking everything now - earnings, miles, expenses - because it's incredibly easy to cross $400 without realizing it, especially if you pick up any other gig work. I made the mistake of not tracking my miles properly when I first started, thinking I'd stay under the threshold. Ended up going over $400 by December and had to scramble to reconstruct my mileage records. Trust me, it's much easier to track from day one than to try to piece it together later! Also keep in mind that even if Doordash doesn't report your earnings to the IRS via 1099, they still have records of all payments made to you. During an audit, the IRS can request those records directly from the company. It's always better to be proactive about tax compliance, especially since proper deduction tracking often means you'll owe less (or even get money back) than you expect.

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Aisha Khan

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This is exactly the kind of real-world experience I needed to hear! I'm in such a similar situation - also a college student trying to figure out gig work taxes for the first time. Your point about tracking everything from day one really resonates with me. I've been kind of lazy about it so far, just checking my earnings in the Doordash app occasionally, but you're right that $400 can sneak up on you faster than expected. I'm curious - when you had to reconstruct your mileage records, how did you go about it? Did you use your Google Maps history or something like that? I'm worried I might already be behind on tracking since I've done about 15 delivery shifts without keeping detailed records. Also, did you end up owing taxes or did the mileage deduction actually help you break even? Thanks for the heads up about the audit risk too. I hadn't really thought about the fact that Doordash keeps records of everything even if they don't send me a 1099. Definitely motivates me to get organized and do this right from the start!

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Amina Diop

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I'm an accountant and handle this situation all the time with clients. Here's a simple checklist for unused LLCs: Federal: If single-member (disregarded entity), no separate federal filing needed. If multi-member or elected corporate taxation, file returns showing zero activity. State Income Tax: Varies dramatically by state. Some require returns regardless of activity. State Franchise/Privilege Tax: Many states charge these regardless of income (CA's $800 minimum is notorious). Annual Reports: Often required by Secretary of State offices regardless of activity. Honestly, between state fees, franchise taxes, and filing requirements, an unused LLC usually costs more trouble than it's worth. I typically advise clients to dissolve unused entities and form a new one when they're actually ready to start the business.

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NightOwl42

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Thank you for laying this out so clearly! I think I'll probably just dissolve mine since I'm not going to use it anytime soon. Sounds like it's just going to be a money drain otherwise.

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Anna Stewart

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As someone who went through this exact situation last year, I'd definitely recommend getting professional advice before making the dissolution decision. I almost dissolved my unused LLC thinking it was just costing me money, but my accountant pointed out that if I planned to start any business in the next few years, keeping it might actually save money in the long run. Formation fees, registered agent costs, and the time to set everything up again can add up. Plus, some states have "shelf life" restrictions where you can't reuse certain business names for a period after dissolution. If you're truly done with business plans, dissolve it. But if there's any chance you'll want to start something in the next 2-3 years, it might be worth keeping and just staying compliant with the minimal requirements.

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Sophie Duck

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That's a really good point about the shelf life restrictions! I hadn't thought about that at all. Do you know if there's a typical timeframe most states use for name restrictions after dissolution? I'm in Illinois and was leaning toward dissolving, but now I'm wondering if I should just bite the bullet and pay the annual fees to keep it active since I might want to start something in a year or two.

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