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This thread has been incredibly helpful! I'm in a similar situation as the original poster - had some good luck with sports betting apps this year and realized I have no idea what I'm doing tax-wise. One question I haven't seen addressed: what happens if you have a really good year gambling but then lose most of it back in the following tax year? Like if I win $15,000 in 2024 but then lose $12,000 of it in early 2025, I still have to pay taxes on the full $15,000 for my 2024 return, right? Those 2025 losses can't offset the 2024 winnings? Also, for anyone using the betting apps - do they automatically send you tax forms at the end of the year if you hit certain thresholds, or do you have to request your win/loss statements? I've been pretty lucky on FanDuel and DraftKings but haven't gotten any tax documents yet. Thanks to everyone who's shared their experiences here, especially about the record-keeping requirements. Definitely going to start taking screenshots of everything going forward!
You're absolutely right about the tax year issue - each tax year stands alone, so those 2025 losses unfortunately can't offset your 2024 winnings. You'll owe taxes on the full $15,000 for 2024, then you can use the 2025 losses to offset any 2025 winnings (if you itemize that year). This is one of the trickier aspects of gambling taxes that catches people off guard. For the betting apps, they typically send 1099-MISC forms if you have net winnings of $600 or more AND the winnings are at least 300 times your wager. But even if you don't get forms, you're still required to report all winnings. Most apps will provide year-end statements if you log into your account, and I'd recommend downloading those regardless of whether you get official tax forms. Since you mentioned FanDuel and DraftKings specifically, both have tax document sections in their apps where you can access your annual statements. Just search for "tax" or "1099" in the app settings. Definitely start that screenshot habit now - you'll thank yourself later!
Something I want to add that hasn't been covered much - if you're gambling across multiple platforms and casinos, you'll want to consolidate all your records early in the process rather than waiting until tax time. I made the mistake of keeping separate logs for each app and casino, thinking I'd combine them later. Come April, I had scattered records across 4 different betting apps, 2 casinos, and a bunch of handwritten notes from poker games. Trying to reconcile everything into one coherent picture was a nightmare, especially when some dates didn't match up between my bank statements and my gambling logs. Now I update one master spreadsheet every week with all activity from all sources. It takes about 15 minutes but saves hours of headache later. I also take a photo of any physical tickets or receipts immediately and upload them to a dedicated folder on my phone. The key is building the habit before you really need it. When you're having a good run and winning regularly, it's easy to think you'll remember everything or that you'll "figure it out later." Trust me - you won't, and it becomes exponentially harder to reconstruct accurate records as time goes on.
This is excellent advice about consolidating records! I'm just getting started with gambling and already feeling overwhelmed by trying to track everything across different platforms. Your weekly update system sounds really manageable. Quick question - when you're updating your master spreadsheet, do you include the pending bets that haven't settled yet, or only the final results? I have some sports bets that won't resolve for a few weeks and I'm not sure whether to log them now or wait until they're official. Also, for the photo storage system, are you keeping those images indefinitely or is there a reasonable timeframe where you can delete older ones? I really appreciate everyone sharing their real experiences here instead of just generic tax advice. It's helping me avoid what sounds like some pretty costly mistakes!
Just want to add some clarity on the timing aspect that might be helpful. Since you mentioned the sale occurred in February 2023 and you're still working on the 1041, make sure you're aware that the capital loss from the selling expenses will be reported on the 1041 for the tax year when the sale occurred (2023), not when you file the return. Also, if this is the final 1041 for the estate, any unused capital losses will pass through to the beneficiaries on their K-1s. But if the estate continues beyond 2023, the losses would first offset any capital gains the estate might have in future years before passing through. One practical tip: when you prepare the K-1s for beneficiaries, make sure to include a statement explaining the nature of the capital loss so they understand it came from selling expenses on the residence. This helps them (and their tax preparers) properly report it on their personal returns.
This is excellent advice from everyone here. I'm currently dealing with a similar situation as the executor of my grandmother's estate. One additional consideration that hasn't been mentioned - if the estate has other capital gains from stock sales or other assets, those gains can offset the capital loss from the property sale before the loss passes through to beneficiaries. In my case, we had about $15K in capital gains from selling stocks and the $22K loss from selling the house (after commissions and legal fees). The net $7K capital loss will pass through to the beneficiaries on their K-1s rather than the full $22K loss. Also, make sure to keep detailed records of all selling expenses - not just the obvious ones like realtor commissions. Title insurance, transfer taxes, repairs needed for sale, staging costs, and even utilities during the marketing period can all be legitimate selling expenses that reduce your proceeds and increase the deductible loss. The timing Sofia mentioned is crucial too. Since your sale was in February 2023, that loss needs to be reported on the 2023 estate return, even if you're filing it now in 2024.
This is really helpful information about offsetting gains and losses within the estate before passing through to beneficiaries. I hadn't considered that aspect. Quick question - do you know if there's a specific order for how different types of gains and losses are matched? For example, if we have both short-term and long-term capital gains from other asset sales, does it matter which ones offset the long-term loss from the property sale? I want to make sure I'm calculating the pass-through amounts correctly for the beneficiaries' K-1s.
I'm sorry you're going through this difficult situation! Unfortunately, everyone here is correct - you cannot claim your ex-wife as a dependent even though you provided most of her financial support. The IRS specifically excludes former spouses from qualifying as dependents, regardless of the support amount or income thresholds. Since you don't have any qualifying dependents (like children or other relatives living with you), you'll need to file as single rather than head of household. I know this doesn't reflect the financial reality of your situation, but the tax code is quite rigid on these points. A few suggestions to help minimize your tax burden: maximize any retirement account contributions you can still make for the tax year, ensure you're taking the standard deduction ($13,850 for single filers in 2023), and look into any other legitimate deductions like charitable contributions or state/local taxes if you itemize. Since you're preparing both returns, be extra careful to avoid any conflicts or duplicate claims that could trigger IRS scrutiny. Consider having a tax professional review both returns before filing, especially given the coordination required and your unique post-divorce support arrangement. It's really commendable that you're continuing to support your ex-wife during her transition, even without tax benefits!
This is such great comprehensive advice! I really appreciate how you've summarized all the key points from this discussion. The retirement contribution strategy seems like it's going to be my best bet for reducing the tax impact this year, especially since I can't get the dependent exemption I was hoping for. I think having a professional review both returns is definitely the way to go - there are too many potential coordination issues and I don't want to accidentally create problems with the IRS. It's been really eye-opening to learn how strict these rules are around ex-spouses, even when you're genuinely providing financial support. Thanks to everyone in this thread for helping me understand what I need to do!
I've been following this thread and wanted to add one more perspective that might be helpful. While everyone is absolutely correct about the ex-spouse dependency rules, I went through a similar post-divorce financial situation and found that keeping detailed records of all the support I provided was actually valuable for other reasons beyond taxes. Even though you can't claim your ex-wife as a dependent this year, if your support arrangement continues and circumstances change (like if she moves in with you permanently or if there are future legal considerations), having documented proof of the financial support could be important. Courts sometimes consider ongoing support patterns in modification hearings, and it demonstrates good faith if any disputes arise later. Also, since you mentioned she only made $4,800 for the year, make sure when you prepare her return that you're not missing any credits she might qualify for as a low-income taxpayer - things like the Earned Income Tax Credit could be valuable for her individual situation, even if it doesn't help your return. It really sounds like you're handling a difficult situation with a lot of care and responsibility, even though the tax code isn't giving you the recognition you deserve for supporting her transition.
This is really thoughtful advice about keeping detailed records! I hadn't considered the potential legal benefits of documenting all the support I've provided, even though it doesn't help with taxes this year. You're absolutely right that having that paper trail could be valuable if circumstances change or if any legal issues come up later. The point about making sure I maximize credits on her return is really good too - I've been so focused on my own tax situation that I hadn't thought much about optimizing her filing. Since she only made $4,800, she might qualify for some low-income credits that could really help her financially. I'll definitely look into the Earned Income Tax Credit and other potential benefits when I prepare her return. It's nice to hear from someone who went through a similar situation and found ways to make the best of it, even when the tax rules don't work in your favor. Thanks for the practical perspective on documentation and for thinking about both sides of this filing situation!
The timing confusion you're experiencing is really common! Since you spent the money in 2023 but didn't start generating income until 2024, you'll want to take the startup cost deduction on your 2024 tax return. The IRS considers your business to have "begun operations" when you first started providing services and earning income, not when you incurred the expenses. So you can deduct up to $5,000 of your startup costs directly on your 2024 return, and the remaining $2,200 would need to be amortized over 15 years starting in 2024. Don't amend your 2023 return - that would actually be incorrect since your business wasn't considered "active" yet according to IRS definitions. Make sure to keep all your receipts from 2023 as documentation for these startup expenses, even though you're claiming them in 2024. The key is when your business began operating, not when you paid for the expenses.
This is really helpful clarification! I was in a similar boat with my freelance graphic design business - had all these setup expenses in one year but didn't land my first paying client until the following year. It's counterintuitive that you claim the deduction when you start earning, not when you spend, but it makes sense from the IRS perspective since that's when your business is actually "in operation." Thanks for explaining the $5k immediate deduction vs 15-year amortization split too - I didn't realize there was that threshold!
This is such a great question and the answers here are really solid! I went through the exact same confusion with my consulting business last year. One thing that might help clarify - the IRS Publication 535 has a section specifically on startup costs that breaks down the timing rules pretty clearly once you know what to look for. The key phrase is "begins business operations" which they define as when you start the activities for which your business was organized - so in your case, when you first started doing paid photography work in 2024. Even though you spent the money preparing in 2023, the deduction goes on your 2024 return. Also worth noting - keep excellent records of all those 2023 expenses because if you ever get audited, you'll need to prove both the amount and that they were legitimate startup costs. The IRS can be pretty strict about what qualifies versus what they consider personal expenses or regular business costs.
Great point about Publication 535! I'm just getting started with understanding business taxes and that publication has been really helpful. One question - when you mention keeping "excellent records," what specific documentation should someone save beyond just the receipts? I have receipts for everything but I'm wondering if there are other documents I should be holding onto to prove these were legitimate startup expenses if the IRS ever asks.
Aisha Abdullah
My husband and I just went through an IRS audit for exactly this situation! Big warning: we ran into trouble because we were renting out too much of our home. The IRS agent cited the "dwelling unit used as a home" rules and said we were treating it more as a rental property than a personal residence. The key is making sure your personal use days exceed the greater of: 14 days or 10% of the total days it's rented. So if you rent portions of your home for 300 days, you need to personally use it for at least 30 days during the year. For duplicate expenses, keep detailed records showing you're paying both housing costs (mortgage/utilities at your tax home AND temporary housing during assignments). The IRS was particularly interested in seeing that we maintained utility services in our name even during rental periods. Also, a lot of travel nurse agencies don't handle state taxes correctly! Double-check their withholding - ours completely missed withholding for two states which created a mess.
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Ethan Davis
ā¢This is why tax rules make no sense! So if they rent out parts of their home for 300 days but are only physically there for say, 25 days, they fail the test? Even though they maintain a portion for themselves year-round? That seems crazy strict.
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Aisha Abdullah
ā¢Actually, that's a common misunderstanding. The personal use days calculation is tricky for partial rentals. Since they're maintaining a portion of the home for their exclusive use year-round, those days count as personal use days even when they're physically away. So in your example, they'd likely pass the test. What tripped us up was that we rented our ENTIRE home with no space reserved for ourselves, then counted just the days we were physically there as personal use. The IRS ruled that we had effectively converted it to a rental property. Big difference when you maintain a specific portion exclusively for yourself!
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Natalie Adams
This thread has been incredibly helpful! I'm a travel PT who's been struggling with similar tax home issues. One thing I'd add based on my experience - document EVERYTHING about your intent to return permanently to your tax home. The IRS looks closely at whether you truly intend your travel assignments to be temporary. Keep records showing you're actively planning your return: renewal of professional licenses in your home state, maintaining voter registration, keeping your kids enrolled in local schools if applicable, continuing relationships with local healthcare providers, etc. Also, for the state tax filing complexity you mentioned - I learned the hard way that some states have "convenience of employer" rules that can trip up remote workers. New York is notorious for this. Your husband should definitely check if any of the states you'll be in have these rules, as they might try to tax his entire income even if he's just temporarily there with you. One last tip: consider getting a tax professional who specializes in itinerant workers BEFORE you start traveling. The upfront cost pays for itself when you avoid mistakes that could trigger an audit or penalties later.
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Emma Bianchi
ā¢This is such valuable advice, especially about documenting intent to return! I hadn't thought about the "convenience of employer" rules - that could definitely complicate things for remote workers. Quick question for everyone who's been through this - how important is it to maintain the same bedroom/space in your home throughout the travel period? We were thinking of switching which room we keep for ourselves based on rental demand, but now I'm wondering if that consistency matters to the IRS for proving it's truly our permanent residence? Also, has anyone dealt with property management companies for the rental portion while traveling? I'm worried about losing control over documentation and record-keeping if we use a third party to handle the rentals.
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